EP2687586A1 - Use of defined cyclohexenones as a means for the additive reinforcement of a smell impression and composition of aromas and/or tastes - Google Patents

Abstract

Use of cyclohex-2-enone compound (I) or a mixture comprising two, three, four, five, six or different compounds (I), for the superadditive enhancement of an olfactory impression, is claimed. Use of cyclohex-2-enone compound of formula (I) or a mixture comprising two, three, four, five, six or different compounds of formula (I), for the superadditive enhancement of an olfactory impression, is claimed. R1, R2, R6 : H, methyl or ethyl; R3 : H, methyl, ethyl or isopropyl; R4 : H, methyl, ethyl, n-propyl or isopropyl; R5 : H or methyl; and R6 : H, methyl or ethyl, provided that R1 is not methyl or ethyl, when R6 is methyl or ethyl. Independent claims are included for: (1) the compound (I); (2) a fragrance and/or flavor material composition comprising (a) (I), and (b) one or more compounds not comprising (I), where at least one of the compounds not comprising (I) has one or both of a floral and fruity odor; and (3) preparation of (I). [Image].

Description

oder einer Mischung bestehend aus oder umfassend zwei, drei, vier, fünf, sechs oder mehr verschiedenen Verbindungen der Formel (I) zum überadditiven Verstärken eines Geruchseindrucks. Die Reste R1 bis R6 haben die nachfolgend definierte Bedeutung.The present invention relates to the use of a compound of the formula (I)

or a mixture consisting of or comprising two, three, four, five, six or more different compounds of formula (I) for over-additive enhancing an odor impression. The radicals R 1 to R 6 have the meaning defined below.

The invention also relates to novel fragrance and / or flavor compositions which, in addition to a compound of formula (I) or a mixture thereof, as described herein, one, two, three, or more other fragrances and / or flavors, wherein the or the other fragrances and / or flavorings are not compounds of the formula (I).

Furthermore, the present invention relates to perfumed and / or flavored articles containing a corresponding fragrance and / or flavor mixture according to the present invention.

Furthermore, the present invention relates to perfumed and / or flavored articles containing a corresponding fragrance and / or flavor mixture according to the present invention.

The present invention also relates to processes for the preparation of a compound of the formula (I) and to a process for the over-additive strengthening of an odor impression.

Finally, the invention also relates to novel, particularly advantageous compounds of the formula (I) and corresponding mixtures. In addition, the use of said new compounds is described as a fragrance, flavoring agent or means for over-additive enhancing an odor.

Further aspects of the present invention will become apparent from the following description, the examples and in particular the appended claims.

In the fragrance industry, there is a continuing need to emphasize (emphasize) and / or over-additive certain odor aspects of a fragrance and / or flavor or perfume and / or flavor mixture. In particular, there is always a need to emphasize (emphasize) and / or over-additive to emphasize floral and / or fruity odor impressions of fragrances and / or flavorings or fragrance and / or flavor mixtures.

• einer Verbindung der Formel (I)
  
  oder
• einer Mischung bestehend aus oder umfassend (vorzugsweise bestehend aus) zwei, drei, vier, fünf, sechs oder mehr verschiedenen Verbindungen der Formel (I),

wobei in jeder der Verbindungen der Formel (I) die Reste R1, R2, R3, R4, R5 und R6 jeweils unabhängig voneinander die folgende Bedeutung haben

• R1 bedeutet Wasserstoff, Methyl oder Ethyl,
• R2 bedeutet Wasserstoff, Methyl oder Ethyl,
• R3 bedeutet Wasserstoff, Methyl, Ethyl oder Isopropyl,
• R4 bedeutet Wasserstoff, Methyl, Ethyl, n-Propyl oder Isopropyl,
• R5 bedeutet Wasserstoff oder Methyl,
• R6 bedeutet Wasserstoff, Methyl oder Ethyl,
• mit der Maßgabe, dass R1 nicht Methyl oder Ethyl ist, wenn R6 Methyl oder Ethyl ist,
• zum überadditiven Verstärken eines Geruchseindrucks.

The object of the present invention was to overdidify certain odor aspects of fragrances and / or flavorings or odoriferous and / or flavoring mixtures. This task is solved by the use

• a compound of the formula (I)
  
  or
• a mixture consisting of or comprising (preferably consisting of) two, three, four, five, six or more different compounds of the formula (I),

wherein in each of the compounds of formula (I) the radicals R1, R2, R3, R4, R5 and R6 each independently have the following meaning

• R1 is hydrogen, methyl or ethyl,
• R2 is hydrogen, methyl or ethyl,
• R3 is hydrogen, methyl, ethyl or isopropyl,
• R4 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
• R5 is hydrogen or methyl,
• R6 is hydrogen, methyl or ethyl,
• with the proviso that R1 is not methyl or ethyl when R6 is methyl or ethyl,
• for over-additive strengthening of an odor impression.

An olfactory impression is an odor impression that can be described by one or more descriptors. In the context of the present text, such odor impressions are particularly relevant, which can be described by one or more descriptors, which are selected from the group consisting of floral and fruity.

A superadditive enhancement of an odor impression (also referred to as a synergistic enhancement of an odor impression) is understood to mean the effect by adding the compound of the formula (I) to one, two, three or more further fragrances and / or flavorants, wherein the or the other odoriferous and / or flavoring substances are not compounds of the formula (I), an odor impression is obtained which is stronger than the sum of the individual odor sensations. If, for example, a (further) olfactory and / or flavoring substance has a fruity or floral olfactory impression (besides possibly further olfactory impressions), there is a superadditive enhancement of the olfactory impression if the fruity or overall floral odor impression of the resulting mixture comprises the compound of the formula (I) and the (further) olfactory and / or flavoring agent is stronger than the sum of the floral or fruity olfactory impressions of on the one hand the compound of formula (I) and on the other hand the (further) olfactory and / or flavoring.

In the context of the present invention, novel compounds of the above formula (I) and corresponding mixtures have also been found. Such are described below.

• Die Mechanismen der Geruchswahrnehmung sind (noch) nicht ausreichend bekannt.
• Die Zusammenhänge zwischen der speziellen Geruchswahrnehmung einerseits und der chemischen Struktur des zugehörigen Riechstoffs andererseits sind (noch) nicht hinreichend erforscht.
• Häufig bewirken bereits geringfügige Änderungen am strukturellen Aufbau eines bekannten Riechstoffs oder eines Mittels zum überadditiven Verstärken eines Geruchseindrucks, starke Änderungen der sensorischen (oder anderer) Eigenschaften. Diese können zudem die Verträglichkeit für den menschlichen Organismus beeinträchtigen.
• Der Mechanismus zum Verstärken von Geruchseindrücken ist (noch) nicht ausreichend erforscht. Somit kann keine Voraussage getroffen werden, ob und wann eine Verbindung in der Lage ist, einen Geruchseindruck einer anderen Substanz zu verstärken.

It was particularly surprising that the compounds of formula (I) described herein are particularly suitable for the purposes of the present invention. Because the search for suitable means for over-additive intensification of an odor impression was - and is usually - made difficult by the following circumstances:

• The mechanisms of smell perception are not (yet) sufficiently known.
• The connections between the special smell perception on the one hand and the chemical structure of the corresponding fragrance on the other hand are not (yet) adequately researched.
• Often, even minor changes in the structural design of a known perfume or agent to enhance overdimensional enhancement of an odor impression cause significant changes in sensory (or other) properties. These can also affect the tolerability of the human organism.
• The mechanism for enhancing olfactory impressions is not (yet) sufficiently researched. Thus, no prediction can be made as to whether and when a compound is capable of enhancing an odor impression of another substance.

It is unpredictable how, on the basis of a given basic structure, structural changes can be attributed to the interactions of a particular compound with other fragrances or flavorings whose odor is e.g. should be strengthened. Unpredictable are thus the resulting sensory (and possibly also further) properties of a corresponding fragrance and / or flavoring composition.

Depending on the meaning of the radicals R 1 to R 6 in the compound of the formula (I), different stereocenters may be present in the compound of the formula (I). A compound of the formula (I) or mixtures thereof can in each case be present as pure configuration isomers in which all stereocenters have the identical constitution, or as mixtures of configurational isomers. If a mixture of different isomers is present, this mixture is not referred to in the context of the present text as a mixture, provided that the radicals R1 to R6 have the same meaning in the configuration isomers.

Surprisingly, some of the compounds of the formula (I) or mixtures thereof have particularly pronounced properties for the over-additive enhancement of an odor impression. Accordingly, the use according to the invention of a single compound or a mixture is particularly preferred, wherein the individual compound of the formula (I) or one, several or all compounds of the formula (I) is selected or are each independently selected from the group consisting of the following compounds (1) to (61), preferably selected from the group consisting of the compounds (2), (4), (13), (23), (29) and (43):

It has surprisingly been found that the compound of the formula (I) or a mixture consisting of or comprising two, three, four, five, six or more different compounds of the formula (I) as described above, especially floral and / or fruity olfactory impressions, are superadditive can amplify. A use according to the invention as an odor enhancer for over-additive intensification of floral and / or fruity odor impressions is therefore particularly preferred.

By using the compound of the formula (I) or a mixture consisting of or comprising two, three, four, five, six or more different compounds of the formula (I) as described above, the resulting odor can already be introduced in small doses. and / or flavoring compositions over-additive to enhance floral and / or fruity scents, with the overall odor impression generally strikingly harmonized and the radiation are perceptibly increased (see Example 42).

The compound of the formula (I) or a mixture consisting of or comprising two, three, four, five, six or more different compounds of the formula (I) are suitable excellent as a means for over-additive enhancing an odor impression, in particular a floral and / or fruity odor impression.

In resulting compositions, some odor impressions are often not beneficial. Accordingly, a use according to the invention is particularly preferred wherein the odor impression to be amplified is not selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spiced and / or wherein the compound of formula (I) or the corresponding mixture (as just defined) does not impart any odor impression selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spicey.

A person skilled in the art will find in an inventive use of a compound of formula (I) or a mixture consisting of or comprising two, three, four, five, six or more different compounds of formula (I), the proportion of the compound of formula (I) or the mixture of the compounds of formula (I) so that the desired effect of the over-additive strengthening of an olfactory note is achieved, wherein it preferably takes care, on the one hand not too large amounts of the compound of formula (I) or the mixture of the compounds Use formula (I), which could dominate the overall sensory impression of an emerging olfactory and / or flavor composition and on the other hand not only so small amount of the compound of formula (I) or the mixture of the compounds of formula (I) provide that a gain odor aspects is not felt or not to a significant extent. Of course, since the compounds of formula (I) used for over-additive amplification may have an inherent odor, it is also possible to exploit this inherent odor of the compounds of formula (I) in a fragrance and / or flavor composition (as described below) In addition to the desired effect of the over-additive strengthening of an odor note, the inherent odor of the compound of the formula (I) used also comes into its own.

In view of the state of the art, it was particularly surprising that it was now possible to identify new, particularly valuable means for over-additive intensification of an odor impression. In addition, the compounds of the formula (I) to be used according to the invention, in particular the novel compounds of the formula (I), have independent olfactory properties. In particular, the new compounds of the formula (I) have odor notes which are surprising, see below. An odor-enhancing effect of the compounds of the formula (I) to be used according to the invention has not yet been described.

A selection of known cyclohexenones is summarized below:

• Livescone (ii),
• Substanzen (iii) und (iv) ( Federal Register 1967, 32, 7946 ),
• Isophoron (v, R = Me),
• Crypton (vi) ( DE 2551172 A1 ),
• Carvotanaceton (vii) ( J. Chem. Soc., Trans. 1898, 73, 852 ),
• Piperitone (viii) und
• Seudenone (ix).

Known cyclohexenones with already known sensory properties are:

• Live scones (ii),
• Substances (iii) and (iv) ( Federal Register 1967, 32, 7946 )
• Isophorone (v, R = Me),
• Crypton (vi) ( DE 2551172 A1 )
• Carvotanacetone (vii) ( J. Chem. Soc., Trans. 1898, 73, 852 )
• Piperitone (viii) and
• Seudenone (ix).

The organoleptic properties of Compound (ix) (Seudenone) are described in Perfumer & Flavorist 1998, 23, 56 described as sweet, nutty, phenolic, walnut, fruity and almond.

In DE 25 511 72 A1 becomes compound (2) (as described above) as strong, balsamic, woody, licorice-like, slightly fruity, in DE 36 40 591 A1 Compound (3) described as sweet, herbaceous, with anise note and compound (4) as flowery, herbaceous, sweetish, woody. In our own investigations, it has surprisingly been found that compound (2) has an odor, as in DE 25 511 72 A1 not described. The smell description is according to our own investigations: fresh, sweet, spicy, aromatic, fruity, grapefruit, vermouth. (Compare Example 2).

In Liebigs Ann 1911, 379, 215 the substance (3) is described as pinocarvonartig (according to S. Arctander, Perfume and Flavor Materials: camphrig, minty).

In Chem. Ber. 1948, 81, 197 Compound (30) is described as having a terpene-like odor.

In J. Econ. Entomol. 1971, 64, 970 describes the use of compound (ix) as an attractant for bark beetle.

Compounds of the general formula (v) (isophorone when R = Me) are described in WO 8500096 A1 described as a repellent for birds.

Some compounds of the general formula (I) are known as starting materials or intermediates for or in various reactions, without that odor or taste properties are described. For example, compound (5) is used for the preparation of benzoquinones ( Org. Biomol. Chem. 2005, 3, 3479 ), Compounds (8) and (13) are formed upon acid-catalyzed rearrangement of camphor ( Tetrahedron 1976, 32, 1699 ) and Carvomenthon ( Soc. Soc. Chim. Fr. 1978, 255 ). By alpha-alkylation of isophorone ( Compt. Rend. 1953, 237, 910 ) or isophorone carboxylate ( Soc. Soc. Chim. Fr. 1954, 690 ) one arrives at the compounds (29) and (30) which are used inter alia as starting materials for the preparation of light-sensitive substances ( US 5356769 A ) or for the construction of stereoid frameworks ( J. Am. Chem. Soc. 1993, 115, 504 ) be used. See also the following patent literature: WO 2012041820 A1 . WO 2009066193 A1 . WO 2009044310 A1 . WO 2007135582 A1 . WO 2004000776 A1 . WO 2009039675 A1 . JP 60045544 . JP 60032745 . JP 200302722 A . CH 603071 A5 and US 4418087 A ,

Compounds which do not fall under the general formula (I) but have individual structural similarities with the compounds of the general formula (I) according to the invention can be found in the patent literature listed below: US 4326997 A . US 4326996 A and CH 611159 A ,

In DE 22 57 121 For example, the compounds 5-ethylcyclohexene-2-one and 6-ethylcyclohexene-2-one are used as agents for improving, enhancing or modifying organoleptic Properties described. In addition, cyclohexenones of a general formula II are given as part of a composition which additionally contains at least one pyrazine or pyrazine derivative. Certain cyclohexenones are described as taste modifiers, the taste notes of the respective compounds themselves not being described.

1. (A) eine erfindungsgemäße Verbindung der Formel (I)
   
   oder
2. (B) eine Mischung bestehend aus oder umfassend zwei, drei, vier, fünf, sechs oder mehr verschiedene erfindungsgemäße Verbindungen der Formel (I),

wobei die Verbindung der Formel (I) bzw. eine, mehrere oder sämtliche Verbindungen der Formel (I) ausgewählt ist bzw. jeweils unabhängig voneinander ausgewählt sind aus der Gruppe bestehend aus den folgenden Verbindungen:

• 6-Ethyl-4-isopropylcyclohex-2-en-1-on (1), 5,6-Diethyl-4-methylcyclohex-2-en-1-on (6), 5-Ethyl-4,6-dimethylcyclohex-2-en-1-on (7), 2,5-Diethyl-4-methylcyclohex-2-en-1-on (9), 3-Ethyl-5-methylcyclohex-2-en-1-on (10), 3,6-Diethyl-5-methylcyclohex-2-en-1-on (11), 3-Ethyl-5,6-dimethylcyclohex-2-en-1-on (12), 2,3-Diethyl-5-methylcyclohex-2-en-1-on (14), 6-Ethyl-4,5-dimethylcyclohex-2-en-1-on (16), 4,5,6-Trimethylcyclohex-2-en-1-on (17), 2,4,5-Trimethylcyclohex-2-en-1-on (18), 2-Ethyl-4,5-dimethylcyclohex-2-en-1-on (19), 6-Ethyl-3,5-dimethylcyclohex-2-en-1-on (20), 6-Ethyl-3,4,5-trimethylcyclohex-2-en-1-on (21), 3,4,5,6-Tetramethylcyclohex-2-en-1-on (22), 2,3,4,5-Tetramethylcyclohex-2-en-1-on (23), 2-Ethyl-3,4,5-trimethylcyclohex-2-en-1-on (24), 5,6-Diethylcyclohex-2-en-1-on (25), 5-Ethyl-6-methylcyclohex-2-en-1-on (26), 6-Ethyl-5,5-dimethylcyclohex-2-en-1-on (27), 2-Ethyl-5,5-dimethylcyclohex-2-en-1-on (28), 6-Ethyl-4-methylcyclohex-2-en-1-on (31), 4,6-Diethylcyclohex-2-en-1-on (32), 4-Ethyl-6-methylcyclohex-2-en-1-on (33), 2,4-Diethyl-cyclohex-2-en-1-on (34), 6-Ethyl-3,4-dimethylcyclohex-2-en-1-on (35), 2-Ethyl-3,4-di-methylcyclohex-2-en-1-on (36), 4-Ethyl-5-methylcyclohex-2-en-1-on (37), 4,6-Diethyl-5-methylcyclohex-2-en-1-on (38), 4-Ethyl-5,6-dimethylcyclohex-2-en-1-on (39), 3,6-Diethyl-cyclohex-2-en-1-on (40), 2,3-Diethylcyclohex-2-en-1-on (41), 4-Ethyl-2,5-dimethylcyclo-hex-2-en-1-on (42), 3-Ethyl-5-isopropyl-2-methylcyclohex-2-en-1-on (43), 3,5-Diethyl-2-methylcyclohex-2-en-1-on (44), 3-Ethyl-2-methyl-5-n-propylcyclohex-2-en-1-on (45), 6-Ethyl-5-isopropylcyclohex-2-en-1-on (46), 5-Isopropyl-6-methylcyclohex-2-en-1-on (47), 2-Ethyl-5-isopropylcyclohex-2-en-1-on (48), 6-Ethyl-5-n-propylcyclohex-2-en-1-on (49), 6-Methyl-5-n-propylcyclohex-2-en-1-on (50), 2-Methyl-5-n-propylcyclohex-2-en-1-on (51), 2-Ethyl-5-n-propylcyclohex-2-en-1-on (52), 6-Ethyl-5-isopropyl-3-methylcyclohex-2-en-1-on (53), 5-Isopropyl-3,6-dimethylcyclohex-2-en-1-on (54), 6-Ethyl-3-methyl-5-n-propyl-cyclohex-2-en-1-on (55), 3,6-Dimethyl-5-n-propylcyclohex-2-en-1-on (56), 4-Ethyl-5-n-propylcyclohex-2-en-1-on (57), 4,6-Diethyl-5-n-propylcyclohex-2-en-1-on (58), 4-Ethyl-6-methyl-5-n-propylcyclohex-2-en-1-on (59), 4-Ethyl-2-methyl-5-n-propylcyclohex-2-en-1-on (60) und 2,4-Diethyl-5-n-propylcyclohex-2-en-1-on (61), vorzugsweise ausgewählt sind aus der Gruppe bestehend aus 2,3,4,5-Tetramethylcyclohex-2-en-1-on (23) und 3-Ethyl-5-isopropyl-2-methylcyclohex-2-en-1-on (43).

As described above, the present invention also relates to novel compounds of the formula (I) and to corresponding mixtures. Accordingly, another aspect of the present invention relates

1. (A) a compound of the formula (I) according to the invention
   
   or
2. (B) a mixture consisting of or comprising two, three, four, five, six or more different compounds of the formula (I) according to the invention,

wherein the compound of the formula (I) or one, several or all compounds of the formula (I) is selected or are each independently selected from the group consisting of the following compounds:

• 6-ethyl-4-isopropylcyclohex-2-en-1-one (1), 5,6-diethyl-4-methylcyclohex-2-en-1-one (6), 5-ethyl-4,6-dimethylcyclohexene 2-en-1-one (7), 2,5-diethyl-4-methylcyclohex-2-en-1-one (9), 3-ethyl-5-methylcyclohex-2-en-1-one (10) , 3,6-Diethyl-5-methylcyclohex-2-en-1-one (11), 3-ethyl-5,6-dimethylcyclohex-2-en-1-one (12), 2,3-diethyl-5 -methylcyclohex-2-en-1-one (14), 6-ethyl-4,5-dimethylcyclohex-2-en-1-one (16), 4,5,6-trimethylcyclohex-2-en-1-one (17), 2,4,5-trimethylcyclohex-2-en-1-one (18), 2-ethyl-4,5-dimethylcyclohex-2-en-1-one (19), 6-ethyl-3, 5-dimethylcyclohex-2-en-1-one (20), 6-ethyl-3,4,5-trimethylcyclohex-2-en-1-one (21), 3,4,5,6-tetramethylcyclohex-2 en-1-one (22), 2,3,4,5-tetramethylcyclohex-2-en-1-one (23), 2-ethyl-3,4,5-trimethylcyclohex-2-en-1-one ( 24), 5,6-diethylcyclohex-2-en-1-one (25), 5-ethyl-6-methylcyclohex-2-en-1-one (26), 6-ethyl-5,5-dimethylcyclohex-2 -en-1-one (27), 2-ethyl-5,5-dimethylcyclohex-2-en-1-one (28), 6-ethyl-4-methylcyclohex-2-en-1-one (31), 4,6-diethylcyclohex-2-en-1-one (32), 4-ethyl 1-6-methylcyclohex-2-en-1-one (33), 2,4-diethylcyclohex-2-en-1-one (34), 6-ethyl-3,4-dimethylcyclohex-2-ene 1-one (35), 2-ethyl-3,4-dimethylcyclohex-2-en-1-one (36), 4-ethyl-5-methylcyclohex-2-en-1-one (37), 4 , 6-diethyl-5-methyl-cyclohex-2-en-1-one (38), 4-ethyl-5,6-dimethylcyclohex-2-en-1-one (39), 3,6-diethylcyclohex-2-en-1-one (40), 2,3-diethylcyclohexene 2-en-1-one (41), 4-ethyl-2,5-dimethylcyclohex-2-en-1-one (42), 3-ethyl-5-isopropyl-2-methylcyclohex-2-ene 1-one (43), 3,5-diethyl-2-methylcyclohex-2-en-1-one (44), 3-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one ( 45), 6-ethyl-5-isopropylcyclohex-2-en-1-one (46), 5-isopropyl-6-methylcyclohex-2-en-1-one (47), 2-ethyl-5-isopropylcyclohex-2 -en-1-one (48), 6-ethyl-5-n-propylcyclohex-2-en-1-one (49), 6-methyl-5-n-propylcyclohex-2-en-1-one (50 ), 2-methyl-5-n-propylcyclohex-2-en-1-one (51), 2-ethyl-5-n-propylcyclohex-2-en-1-one (52), 6-ethyl-5 isopropyl 3-methylcyclohex-2-en-1-one (53), 5-isopropyl-3,6-dimethylcyclohex-2-en-1-one (54), 6-ethyl-3-methyl-5-n- propylcyclohex-2-en-1-one (55), 3,6-dimethyl-5-n-propylcyclohex-2-en-1-one (56), 4-ethyl-5-n-propylcyclohex-2- en-1-one (57), 4,6-diethyl-5-n-propylcyclohex-2-en-1-one (58), 4-ethyl-6-methyl-5-n-propylcyclohex-2-ene 1-one (59), 4-ethyl-2-methyl-5-n-propylc cyclohex-2-en-1-one (60) and 2,4-diethyl-5-n-propylcyclohex-2-en-1-one (61), preferably selected from the group consisting of 2,3,4, 5-tetramethylcyclohex-2-en-1-one (23) and 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one (43).

The bracketed numbers after the IUPAC designation of each compound refer to the structural formula given above. If an individual IUPAC name does not correspond to a given structural formula, both listed compounds (according to the structural formula and according to the IUPAC name) should be taken into account.

The novel compounds of the formula (I) and corresponding mixtures are particularly suitable for over-additive intensification of an odor, in particular for over-additive intensification of a floral and / or fruity odor impression.

A mixture (B) according to the invention comprising two, three, four, five, six or more different compounds of the formula (I) according to the invention may be formed in the manner of a fragrance booster concentrate which is intended to be added to base preparations To enhance the odor impression of the base preparation over-additive, for example, with the formation of a particularly valuable olfactory and / or Geschmacksstoffkomposition. Accordingly, a preferred mixture according to the invention comprises no fragrance and / or flavor which is not a compound of the formula (I) as defined above nor a fragrance enhancer which is not a compound of the formula (I) as defined above.

The publication DE 22 57 121 discloses on page 20, with reference to further publications, a number of compounds, namely, cyclohexene-2-one, 2-methyl-cyclohexene-2-one, 3-methylcyclohexene-2-one, 4-methylcyclohexene-2-one, 5-methylcyclo -hexen-2-one, 6-methylcyclohexen-2-one, 2,6-dimethylcyclohexen-2-one, 3,4-dimethylcyclohexen-2-one, 3,5-dimethylcyclohexen-2-one, 3,6 Dimethylcyclohexene-2-one, 4,6-dimethylcyclohexen-2-one, 2,3-dimethylcyclohexene-2-one, 2,4-dimethylcyclohexene-2-one, 2,5-dimethylcyclohexene-2-one , 4,5-dimethylcyclohexene-2-one, 5,6-dimethylcyclohexene-2-one, 2,6-dimethylcyclohexene-2-one, 2-ethylcyclohexene-2-one, 3-ethylcyclohexene-2-one, 4-ethylcyclo hexene-2-one, 5-ethylcyclohexene-2-one and 6-ethylcyclohexene-2-one. The selected name does not always appear correct. The disclosed compounds are no more subject of the present invention than the corresponding compounds disclosed in the underlying publications. Preferably, one, two or more, preferably all compounds of formula (I) in the mixture are not selected from the group of said compounds. A given compound of the formula (I) comprises in many cases several configurational isomers; In the present text, there is no regular language distinction between these configuration isomers. Any reference to a compound of formula (I) comprising a plurality of configurational isomers is herein referred to as referring to each of said configurational isomers as well as referring to each of the conceivable mixtures of two or more (if present) of said configurational isomers to understand. Thus, for example, reference to 6-ethyl-4-isopropylcyclohex-2-en-1-one corresponds to a reference to each of the configurational isomers of 6-ethyl-4-isopropylcycloshex-2-en-1-one, as well as any mixture thereof configurational. In the examples below, specific information on the compounds used or investigated results from the given analytical data.

Surprisingly, it has been shown that the novel compounds of the formula (I) (as described above) each also have a particularly interesting odor and / or taste. This is surprising despite a structural similarity of these new compounds with the known compounds, because from the structure of a known first compound with known sensory properties and their structural similarity to the structure of a second compound can not be concluded on the smell or taste of this second compound. Numerous examples are known from the literature, in which even the slightest variations of the chemical structure (eg, replacement of methyl groups by hydrogen) first odorless substances then have a smell. To the impossibility of smell prediction please refer CS Sell, Angew. Chem. 2006, 118, 6402 , Therefore, in the present situation, it is surprising that the novel compounds of the formula (I) have an odor and / or taste and that this odor and / or taste has independent organoleptic, in particular olfactory and / or gustatory, properties which differ significantly from stand out from the known compounds and even surpass them. In particular, the odor notes spicy, saffron, coumarin, aromatic, leather and / or tobacco frequently found in the new compounds differ greatly from the odor notes known from the prior art for cyclohex-2-en-1-one compounds.

The present invention thus also relates to the use of the corresponding compounds (1), (2), (3), (4), (5), (8), (9), (10), (12), (13) , (14), (15), (18), (19), (23), (24), (28), (29), (30), (31), (32), (33), ( 34, 37, 40, 41, 42, 43, 44, 45, 48, 51, 52, 57, 60. and (61) as a fragrance having one, two, three, four, five or all of the odor notes selected from the group consisting of anise, spicy, saffron, coumarin, aromatic, leather and tobacco.

Particularly preferred is the combined, i. simultaneous use of the compounds (1), (2), (3), (4), (5), (8), (9), (10), (12), (13), (14), (15 ), (18), (19), (23), (24), (28), (29), (30), (31), (32), (33), (34), (37) 40, 41, 42, 43, 44, 45, 48, 51, 52, 57, 60 and 61 for over-additive amplification an odor impression (preferably for over-additive enhancing a floral and / or fruity odor impression) and as a fragrance with one, two, three, four, five or all odor notes selected from the group consisting of spicy, anise, saffron, coumarin, aromatic, leather and tobacco ,

Surprisingly, some of the new compounds, in particular the compounds described above as being preferred, have a particularly valuable spicy odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (2), (3), (4), (5), (8), (9), (10), (12), (13), (14) , (18), (19), (23), (24), (28), (29), (30), (32), (33), (34), (42), (43), ( 44), (45), (48), (51), (57) and (61) as a fragrance with a spicy note.

Surprisingly, some of the new compounds, in particular the compounds described above as being preferred, have a particularly valuable saffron odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (4), (9), (12), (13), (14), (19), (23), (24), (28), (41) and (30) as a fragrance with a saffron note.

Surprisingly, some of the new compounds, in particular the compounds described above as being preferred, have a particularly valuable coumarin odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (8), (15), (18) and (34) as a fragrance with a coumarin note.

Surprisingly, some of the new compounds, in particular the compounds designated above as preferred, have a particularly valuable aromatic odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (2), (8), (9), (10), (18) and (42) as a fragrance with an aromatic note.

Surprisingly, some of the new compounds, in particular the compounds described above as being preferred, have a particularly valuable leather odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (13), (23), (29), (30), (43) and (44) as a fragrance with a leather note.

Surprisingly, some of the new compounds, in particular the compounds designated above as preferred, have a particularly valuable tobacco odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (9), (15), (23), (24), (29), (30), (40), (41), (43) and (44) as a fragrance with a tobacco note.

Surprisingly, some of the new compounds, in particular the compounds described above as being preferred, have a particularly valuable green odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (1), (12), (13), (31), (34), (43) and (45) as a fragrance with a green note.

Surprisingly, some of the new compounds, in particular those referred to above as preferred, have a particularly valuable anise odor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (9), (45), (51), (52), (57), (60) and (61) as a fragrance with an aniseed note.

Surprisingly, some of the compounds of the formula (I), in particular of the novel compounds of the formula (I) designated above as preferred, have a particularly valuable flavor, in particular a flavor selected from the group consisting of herbaceous, spearmint, cooling, woody, fresh and spicy , see. See the examples below.

The present invention therefore also relates to the use of the compounds of the formula (I) to be used according to the invention as flavoring agents, preferably the compounds of the formula (I) to be used above and / or the novel compounds of the formula (I) according to the invention, preferably as Flavor with a flavor selected from the group consisting of herbaceous, spearmint, cooling, woody, fresh and spicy.

Surprisingly, some of the compounds of the formula (I), in particular of the novel compounds of the formula (I) designated above as being preferred, have a particularly valuable herbaceous flavor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (2), (4) and (43) as a flavoring with a herbaceous note.

Surprisingly, some of the compounds of the formula (I), in particular of the novel compounds of the formula (I) designated above as being preferred, have a particularly valuable spearmint flavor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (2), (29) and (10) as a flavoring with a spearmint note.

Surprisingly, some of the compounds of the formula (I), in particular of the novel compounds of the formula (I) designated above as being preferred, have a particularly valuable cooling taste, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (2) and (23) as a flavoring with a cooling note.

Surprisingly, some of the compounds of the formula (I), in particular of the novel compounds of the formula (I) designated above as being preferred, have a particularly valuable woody flavor note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (4), (13), (23) and (43) as a flavoring with a woody note.

Surprisingly, some of the compounds of the formula (I), in particular of the novel compounds of the formula (I) designated above as being preferred, have a particularly valuable fresh taste note, cf. See the examples below.

The present invention thus also relates to the use of the corresponding compounds (13), (29), (43), (15), (10), (18) and (28) as a flavoring with a fresh note.

Particularly preferred is the combined, i. simultaneous use of the compounds to be used according to the invention for overdixing an odor impression (preferably for over-additive enhancing a floral and / or fruity odor impression) and as a flavoring agent (preferably as a flavoring agent with a note selected from the group consisting of herbaceous, spearmint, cooling, woody, fresh and sharp). For preferred compounds to be used according to the invention, the above statements apply accordingly.

Very particularly preferred is the combined, ie simultaneous use of the compounds (1), (2), (3), (4), (5), (8), (9), (10), (12), (13 ), (14), (15), (18), (19), (23), (24), (28), (29), (30), (31), (32), (33) 34, 37, 40, 41, 42, 43, 44, 45, 48, 51, 52, 57, 60 ) and (61) for over-additive enhancing an odor impression (preferably for over-additive enhancing a floral and / or fruity odor impression) and as a fragrance with one, two, three, four, five or all odor notes selected from the group consisting of spicy, saffron, coumarin , aromatic, leather and tobacco and as a flavoring (preferably as a flavoring with a fresh and / or spicy flavor)

Preferably, the combined, i. simultaneous use of the compounds (1), (2), (3), (4), (5), (8), (9), (10), (12), (13), (14), (15 ), (18), (19), (23), (24), (28), (29), (30), (31), (32), (33), (34), (37) 40, 41, 42, 43, 44, 45, 48, 51, 52, 57, 60 and 61 as a fragrance one, two, three, four, five or all of the odor notes selected from the group consisting of spicy, saffron, coumarin, aromatic, leather and tobacco and as a flavoring (preferably as a flavoring with a fresh and / or spicy note).

Particular preference is given to the use of the compounds of the formula (I) to be used according to the invention, preferably of the compounds of the formula (I) to be used described above and / or of the novel compounds of the formula (I) according to the invention as flavoring agents, wherein the taste note is not a meaty, cereal, chocolate, cocoa, coffee, nutty, sulfuric, earthy and / or greasy flavor.

1. (a) einer Verbindung der Formel (I) oder einer Mischung aus zwei, drei, vier, fünf, sechs oder mehr verschiedenen Verbindungen der Formel (I), wie jeweils oben definiert, vorzugsweise wie jeweils weiter oben bei den erfindungsgemäßen Verbindungen bzw. Mischungen definiert,
   und
2. (b) einem, zwei, drei oder mehr weiteren Riech- und/oder Geschmacksstoffen, wobei der bzw. die weiteren Riech- und/oder Geschmacksstoffe keine Verbindungen der Formel (I) sind.

A further aspect of the present invention relates to fragrance and / or flavor compositions according to the invention, comprising or consisting of

1. (A) a compound of formula (I) or a mixture of two, three, four, five, six or more different compounds of formula (I), as defined above, preferably as in each case above in the compounds or mixtures according to the invention Are defined,
   and
2. (B) one, two, three or more other fragrances and / or flavorings, wherein the other odoriferous and / or flavoring substances are not compounds of formula (I).

As described above in the use according to the invention of a compound of the formula (I) or a mixture of the compounds of the formula (I), the compounds or the mixtures are suitable, in particular, as odor enhancers for the over-additive intensification of a floral and / or fruity odor impression. Accordingly, fragrance and / or flavor compositions according to the invention are particularly preferred in which the or one, two, three, more or all of the other fragrances and / or flavors according to component (b) have a floral and / or a fruity odor.

In resulting fragrance and / or flavor compositions, some olfactory impressions are often not beneficial. Accordingly, an odoriferous and / or flavoring composition according to the invention is particularly preferred, wherein the odor impression of the other odoriferous and / or flavoring ingredients according to constituent (b) to be enhanced is not selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy , toasted, chocolaty and spicy
and or
wherein the compound of formula (I) or the corresponding mixture does not impart an odor impression selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spicey.

This applies correspondingly to mixtures according to the invention which, as stated in some embodiments, comprise, in addition to compounds of the formula (I), further constituents.

Our own investigations have shown that fragrance and / or flavor compositions according to the invention are particularly preferred in which component (b) contains no odoriferous and / or flavoring substances which have a pyrazine base structure.

According to a further preferred aspect of the present invention, fragrance and / or flavor compositions according to the invention are particularly preferred in which component (a) enhances one or more olfactory impressions of component (b), preferably a floral and / or fruity olfactory impression of the component ( b) is strengthened. Such a composition is also referred to as an "odor-enhanced composition"; see. see Examples 37 to 86.

For a fragrance or flavor composition according to the invention (as described above, preferably as preferred above), according to a preferred embodiment, the total amount of compounds of formula (I) is in the range of 0.0001 to 90% by weight, preferably in Range of 0.01 to 70 wt .-%, preferably in the range of 0.1 to 50 wt .-%, particularly preferably in the range of 0.1 to 30 wt .-%, most preferably in the range of 0.1 to 10 wt .-%, based on the total weight of the fragrance and / or flavor composition. An odoriferous or flavoring composition according to the invention which contains compounds of the formula (I) in a total amount of more than 50 to at most 90% by weight is also referred to as an odor-enhancing concentrate and is preferred as such. A fragrance or flavoring composition according to the invention which contains compounds of the formula (I) in a total amount of 0.0001 to 50 wt .-%, is usually a composition in which the total amount of compounds of formula (I) is sufficient, the odor impression of over-additive to reinforce one or more fragrances of component (b) which are not compounds of formula (I). Such a composition is a preferred "odor-enhanced composition"; see. again examples 37 to 86.

Depending on the desired application, it may be advantageous and therefore preferred according to the invention to select the total amount of constituent (a) such that the respectively resulting fragrance and / or flavor composition has no intrinsic odor and / or taste of component (a), but an odor impression , preferably a floral and / or fruity odor impression, at least one, two, three, four, five, six or more of the components of component (b) is enhanced.

Fragrance or flavor compositions according to the invention can be used in liquid form, undiluted or diluted with a solvent for perfuming or flavoring. If the fragrance and / or flavor compositions of the invention are diluted with one or more solvents, the one or more solvents are selected from the group consisting of: ethanol, isopropanol, diethylene glycol monoethyl ether, glycerine, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate , Triethyl citrate, isopropyl myristate, triacetin and vegetable oil.

In addition, it is preferred in individual cases to provide one or more solvents in the odoriferous and / or flavoring compositions according to the invention. These solvents are then preferably selected so that they are physiologically harmless in the individual case concentration. Due to their considerable toxicity, the use of one or more of the following solvents in an odorant and / or flavoring composition according to the invention is not preferred: hexane, toluene, benzene, tetrahydrofuran, pentane, dimethylformamide, diisopropyl ether, Dichloromethane, dichloroethane, chloroform, carbon tetrachloride, N-methylpyrrolidone, pyridine, dimethylacetamide, dimethoxyethane, dioxane, diethyl ether and methanol.

In the context of this invention, compounds of formula (I) (as described above) are not considered as solvents.

It has been shown that further positive properties of the odoriferous and / or flavoring compositions according to the invention are present, as long as the odoriferous and / or flavoring compositions according to the invention comprise corresponding further additives. Suitable additives include: preservatives, abrasives, antiacne agents, anti-aging agents, antibacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, anti-irritants, antimicrobials, antioxidants, astringents, antiperspirants, antiseptic agents, Antistatics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, conditioning agents, depilatory agents, surfactants, deodorizing agents, antiperspirants, emollients, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foaming agents, foam stabilizers, preventing agents foaming, foam boosters, fungicides, gelling agents, gelling agents, hair care products, hair styling agents, hair straighteners, moisturizers, moisturisers, moisturisers, bleaching agents, restoratives, fl corner removing agents, optical brightening agents, impregnating agents, antisoiling agents, friction reducing agents, lubricants, moisturizing creams, ointments, opacifiers, plasticizing agents, occlusive agents, polish, brighteners, polymers, powders, proteins, lubricating agents, abrasives, slilcones, skin soothing agents skin cleansing agents, skin care agents, skin-healing agents, skin-lightening agents, skin-protecting agents, skin softening agents, cooling agents, skin-cooling agents, warming agents, skin-warming agents, stabilizers, UV-absorbing agents, UV filters, detergents, fabric conditioners, suspending agents, skin tanning agents, thickeners, Vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, alpha hydroxy acids, polyhydroxy fatty acids, plasticizers, dyes, color protectants, pigments, anti-corrosives, flavors, flavorings, fragrances, Polyols, surfactants, electrolytes, organic solvents or silicone derivatives. The combination of fragrance and / or flavor compositions and additive according to the invention represents an exemplary article according to the invention.

Furthermore, fragrance and / or flavor compositions of the present invention may be adsorbed to a carrier which provides for both a fine distribution of the odoriferous or flavoring substances in the product as well as a controlled release in use. Such carriers may be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic based substances, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates or polyurethanes. The combination of composition according to the invention and carrier represents an exemplary article according to the invention.

Fragrance and / or flavor compositions, in particular may also be microencapsulated, spray dried, as inclusion complexes or as extrusion products (ie articles according to the invention) and in this form e.g. B. be added to a perfumed or flavored article.

Optionally, the properties of the compositions modified in this way can be further optimized by so-called "coating" with suitable materials with a view to a more targeted release of fragrance, to which end preferably wax-like plastics, such as e.g. Polyvinyl alcohol can be used. The resulting products are in turn articles of the invention.

The microencapsulation of the odoriferous and / or flavoring compositions according to the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, for example of polyurethane-type substances or soft gelatin. The spray-dried fragrance and / or flavor compositions according to the invention can be prepared, for example, by spray-drying an emulsion or dispersion containing the fragrance and / or flavor composition according to the invention, wherein starches, proteins, dextrin and vegetable gums modified as carriers can be used. Inclusion complexes can be prepared, for example, by introducing dispersions of the fragrance and / or flavor composition and cyclodextrins or urea derivatives into a suitable solvent, for example water. Extrusion products can be obtained by fusing the fragrance and / or flavor compositions with a suitable waxy substance and by extrusion with subsequent solidification, optionally in a suitable solvent, for example isopropanol.

The odoriferous and / or flavoring compositions of the invention may be used in concentrated form, in solutions or in modified form as described above for the preparation of perfumed and / or flavored articles of the invention, e.g. Perfume extracts, eau de parfums, eau de toilettes, shaving lotions, eau de colognes, pre-shave products, splash colognes and perfumed tea towels, and the perfuming of acidic, alkaline and neutral detergents, e.g. Floor cleaners, window glass cleaners, dishwashing detergents, bath and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, textile fresheners, ironing aids, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soak and stain removers, fabric softeners, laundry soap, washing tablets, Disinfectants, surface disinfectants and air fresheners in liquid, gel or applied on a solid support form, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe creams and personal care such solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water type cosmetic emulsions such as e.g. Skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, Tanning creams and lotions, hair care products such as Hair sprays, hair gels, hair setting lotions, hair lotions, permanent and semi-permanent hair dyes, hair styling agents such as cold waving and hair straightening agents, hair lotions, hair creams and lotions, deodorants and antiperspirants such as hair wipes. Underarm sprays, roll-ons, deodorants, deodorants, decorative cosmetics, e.g. Eyeshadows, nail polishes, make-ups, lipsticks, mascara and candles, lamp oils, incense sticks, insecticides, repellents and fuels.

The odoriferous and / or flavoring composition according to the invention can be incorporated into flavored or flavored products, in particular nutrition, oral care or pleasure preparations. Such products routinely include ingredients that have functions other than flavor or fragrance development (eg, dyes) and / or are already finished tradable product (eg, perfume oil).

The nutrition or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastries), sweets (eg chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (eg coffee, tea, wine, wine-based beverages, beer, beer-based drinks, liqueurs, brandies, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars) , Fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (eg instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (eg ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or cured meat products) , Eggs or egg products (dry egg, egg whites, egg yolk), cereal products (eg breakfast cereals, granola bars, pre-cooked finished rice products), dairy products (eg milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolyzed milk protein-containing products), soy protein or other soybean products hen fractions (eg soymilk and products made thereof, soy lecithin-containing preparations, fermented products such as tofu or Tempe or products made from it, soy sauces), fruit preparations (eg jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (eg ketchup, sauces, dried vegetables , Frozen vegetables, pre-cooked vegetables, pickled vegetables, cooked vegetables), snack foods (eg baked or fried potato chips or potato dough products, bread dough products, corn or peanut based extrudates), fat and oil based products or emulsions thereof (eg mayonnaise, remoulade, Dressings, spice preparations), other prepared meals and soups (eg dry soups, instant soups, pre-cooked soups), spices, spice mixtures and in particular seasoning seasonings, which are used, for example, in the snack area. After incorporation of the a) inventive compound of formula (I) or the mixture thereof and / or b) of the fragrance and / or flavoring composition according to the invention, these preparations are articles according to the invention.

Preparations may, for. B. present as a semi-finished product or as seasoning mixture.

Preparations may serve, in particular, as semi-finished goods for the production of further preparations serving for nutrition or enjoyment, in particular in spray-dried form. Formulations may also be in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, liquid phase dispersions, emulsions, powders, solutions, pastes or other sip or slurries chewable preparations are present as a dietary supplement.

Oral care preparations are especially oral and / or dental care products such as toothpastes, dental gels, toothpowder, mouthwashes, chewing gums and other oral care products.

Other customary active substances, basic substances, auxiliaries and additives for nutrition, oral care or pleasure-use preparations according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation to be included. Furthermore, the preparations may comprise water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.

The preparations (as examples of articles according to the invention) comprising a) the compound of the formula (I) or its mixture and / or b) the odoriferous and / or flavoring composition according to the invention are prepared according to a preferred embodiment in which the compound according to the invention or their mixtures and / or fragrance and / or flavor composition according to the invention as a substance, as a solution (eg in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (eg maltodextrin, starch, silica gel). , other flavorings or flavorings and, if appropriate, further auxiliaries and / or stabilizers (for example natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic), are incorporated into a basic preparation for nutrition, oral hygiene or pleasure. Advantageously, preparations present as solution and / or suspension or emulsion can also be converted into a solid preparation (semi-finished product) by spray drying.

The spray-dried solid preparations (as an example of inventive article) are particularly suitable as semi-finished goods for the production of further preparations. The spray-dried solid preparations preferably contain 50 to 95% by weight of excipients, in particular maltodextrin and / or starch, 5 to 40% adjuvants, preferably natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic.

According to a further preferred embodiment, for the preparation of preparations a) the compound of the formula (I) or its mixture and / or b) odoriferous and / or flavoring composition according to the invention and optionally other constituents of the preparation according to the invention are initially emulsified, in liposomes, for example starting from phosphatidylcholine, in microspheres, in nanospheres or else in capsules, granules or extrudates from a matrix suitable for foods and luxury foods, for example from starch, starch derivatives (eg modified starch), cellulose or cellulose derivatives (eg hydroxypropylcellulose), other polysaccharides (eg dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan), natural fats, natural waxes (eg beeswax, carnauba wax), from proteins, eg gelatin or other natural products (eg shellac) incorporated. Depending on the matrix, the products may be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally a suitable combination of the abovementioned processes. In a further preferred preparation process for a preparation according to the invention, the compound according to the invention is first complexed with one or more suitable complexing agents, for example cyclodextrins or cyclodextrin derivatives, preferably alpha- or beta-cyclodextrin, and used in this complexed form.

Particularly preferred is a preparation in which the matrix is chosen such that the compound according to the invention is released from the matrix in a delayed manner, so that a long-lasting effect is achieved. In this respect, a fat, wax, polysaccharide or protein matrix is particularly preferred.

As further constituents for the nutrition or the pleasure serving preparations can be used usual basic, auxiliary and additives for food or luxuries, eg water, mixtures of fresh or processed, vegetable or animal basic or raw materials (eg raw, roasted, dried , fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose, glucose , Dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (eg, sorbitol, erythritol), natural or hydrogenated fats (eg, tallow, lard, palm fat, coconut fat, hydrogenated vegetable fat), oils (eg, sunflower oil, peanut oil, corn oil , Olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (eg potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (eg gamma-aminobutyric acid, taurine), peptides (eg glutathione), native or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, taste-correcting agents for unpleasant taste impressions, further taste modulators for other, generally not unpleasant taste impressions, other taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (eg lecithins, diacylglycerols, gum arabic), stabilizers (eg carageenan, alginate ), Preservatives (eg benzoic acid, sorbic acid), antioxidants (eg tocopherol, ascorbic acid), chelators (eg citric acid), organic or inorganic acidulants (eg malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), bitter substances (eg quinine, caffeine, limonin, Amarogentin, humolone, lupolone, catechins, tannins), mineral salts (eg sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), enzymatic tanning substances (eg sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (eg carotenoids , Flavonoids, An thocyanines, chlorophyll and their derivatives), spices, trigeminal active substances or plant extracts, containing such trigeminal active substances, synthetic, natural or nature-identical flavorings or fragrances and odorants.

Dentifrices (as a basis for oral care preparations) containing a) the compound of the invention of the formula (I) or their mixture and / or b) fragrance and / or flavor composition according to the invention generally comprise an abrasive system (grinding or Polishing agents), such as silicas, calcium carbonates, calcium phosphates, Alumiuniumoxide and / or hydroxylapatites, surface-active substances such as sodium lauryl sulfate, Natriumlaurylsarcosinat and / or Cocamidopropylbetain, humectants such as glycerol and / or sorbitol, thickeners such as carboxymethylcellulose, polyethylene glycols, carrageenan and / or Laponite®, sweeteners such as saccharin, flavoring agents for unpleasant taste sensations, flavoring agents for other, generally not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), cooling agents such as menthol, menthol derivatives (eg L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-Trialkylessigsäureamiden (eg 2,2-Diisopropylpropionsäuremethylamid), Icilin and Icilin derivatives, stabilizers and active ingredients, such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, Potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or odor precursors.

Chewing gums (as another example of oral care preparations) containing a) the compound of formula (I) or its mixture and / or b) fragrance and / or flavoring composition according to the invention generally comprise a chewing gum base, i. chewing gum that becomes plastic during chewing, sugar of various types, sugar substitutes, other sweet tasting substances, sugar alcohols, flavoring agents for unpleasant taste impressions, other flavor modulators for further, generally not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or others Substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavors and stabilizers or odor precursors.

The preparations may also contain, in addition to the compound to be used according to the invention, an (additional) aroma composition in order to round off and refine the taste and / or smell of the preparation. Suitable (additional) flavoring compositions include e.g. synthetic, natural or nature-identical flavorings, fragrances and flavorings as well as suitable excipients and carriers.

After incorporation of the a) inventive compound of formula (I) or their mixture and / or b) of the fragrance and / or flavor composition according to the invention, these preparations are articles according to the invention as defined below.

The compounds of the formula (I) to be used according to the invention or corresponding mixtures thereof or a fragrance and / or flavoring composition according to the invention (as described above) can advantageously also be used for perfuming and / or flavoring certain articles or be part of such articles. In particular, a fragrance and / or flavoring composition according to the invention, preferably a fragrance and / or flavoring composition as referred to herein as preferred, can be used within the scope of the present invention as a constituent of a perfumed and / or flavored article.

Accordingly, the present invention also relates to a perfumed and / or flavored article comprising a fragrance and / or flavoring composition (as described herein) according to the invention.

In a preferred embodiment, the perfumed and / or flavored article of the invention is selected from the group consisting of: perfume extracts, eau de parfums, eau de toilettes, shaving waters, eau de colognes, pre-shave products, splash colognes, perfumed towelettes , acidic, alkaline and neutral detergents, textile removers, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, Depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetics, candles, lamp oils, incense sticks, insecticides, repellents and fuels.

Articles according to the invention in many cases comprise a carrier or a substrate which is in direct contact with the compound or compounds of the formula (I) or the odoriferous and / or flavoring composition. Such carriers may be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic based substances, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates or polyurethanes.

• Inkontaktbringen oder Mischen
  • einer Verbindung der Formel (I)
    wie oben definiert, insbesondere wie oben bei den neuen Verbindungen der Formel (I) definiert,
  • einer Mischung aus zwei, drei, vier, fünf, sechs oder mehr verschiedenen Verbindungen der Formel (I),
    wie oben definiert, insbesondere wie oben bei den neuen Verbindungen der Formel (I) definiert,
• oder
  • einer Riech- und/oder Geschmacksstoffkomposition wie oben definiert, mit einem Erzeugnis.

A further aspect of the present invention relates to a method for enhancing an odor impression, preferably a floral and / or fruity odor impression, comprising the following step:

• Contacting or mixing
  • a compound of the formula (I)
    as defined above, in particular as defined above for the novel compounds of the formula (I),
  • a mixture of two, three, four, five, six or more different compounds of formula (I),
    as defined above, in particular as defined above for the novel compounds of the formula (I),
• or
  • a fragrance and / or flavoring composition as defined above with a product.

Preferred products are the above-described preferred articles or preparations according to the invention or one, two, three or more further fragrances and / or flavorings, wherein the other odoriferous and / or flavoring substances are not compounds of the formula (I) and preferably have a floral and / or a fruity odor.

Preferred substances which are or may be contained within the scope of the present invention in an article according to the invention, a fragrance and / or flavoring composition according to the invention, preferably as constituent (b) of a fragrance and / or flavoring composition according to the invention, are found, for example, in US Pat. In S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published , or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001 ,

In detail may be mentioned:

• Ambratinktur; Amyrisöl; Angelicasamenöl; Angelicawurzelöl; Anisöl; Baldrianöl; Basilikumöl; Baummoos-Absolue; Bayöl; Beifußöl; Benzoeresin; Bergamotteöl; Bienenwachs-Absolue; Birkenteeröl; Bittermandelöl; Bohnenkrautöl; Buccoblätteröl; Cabreuvaöl; Cadeöl; Calmusöl; Campheröl; Canangaöl; Cardamomenöl; Cascarillaöl; Cassiaöl; Cassie-Absolue; Castoreum-Absolue; Cedernblätteröl; Cedernholzöl; Cistusöl; Citronellöl; Citronenöl; Copaivabalsam; Copaivabalsamöl; Corianderöl; Costuswurzelöl; Cuminöl; Cypressenöl; Davanaöl; Dillkrautöl; Dillsamenöl; Eau de brouts-Absolue; Eichenmoos-Absolue; Elemiöl; Estragonöl; Eucalyptus-citriodora-Öl; Eucalyptusöl; Fenchelöl; Fichtennadelöl; Galbanumöl; Galbanumresin; Geraniumöl; Grapefruitöl; Guajakholzöl; Gurjunbalsam; Gurjunbalsamöl; Helichrysum-Absolue; Helichrysumöl; Ingweröl; Iriswurzel-Absolue; Iriswurzelöl; Jasmin-Absolue; Kalmusöl; Kamillenöl blau; Kamillenöl römisch; Karottensamenöl; Kaskarillaöl; Kiefernadelöl; Krauseminzöl; Kümmelöl; Labdanumöl; Labdanum-Absolue; Labdanumresin; Lavandin-Absolue; Lavandinöl; Lavendel-Absolue; Lavendelöl; Lemongrasöl; Liebstocköl; Limetteöl destilliert; Limetteöl gepresst; Linaloeöl; Litseacubeba-Öl; Lorbeerblätteröl; Macisöl; Majoranöl; Mandarinenöl; Massoirindenöl; Mimosa-Absolue; Moschuskörneröl; Moschustinktur; Muskateller-Salbei-Öl; Muskatnussöl; Myrrhen-Absolue; Myrrhenöl; Myrtenöl; Nelkenblätteröl; Nelkenblütenöl; Neroliöl; Olibanum-Absolue; Olibanumöl; Opopanaxöl; Orangenblüten-Absolue; Orangenöl; Origanumöl; Palmarosaöl; Patchouliöl; Perillaöl; Perubalsamöl; Petersilienblätteröl; Petersiliensamenöl; Petitgrainöl; Pfefferminzöl; Pfefferöl; Pimentöl; Pineöl; Poleyöl; Rosen-Absolue; Rosenholzöl; Rosenöl; Rosmarinöl; Salbeiöl dalmatinisch; Salbeiöl spanisch; Sandelholzöl; Selleriesamenöl; Spiklavendelöl; Sternanisöl; Styraxöl; Tagetesöl; Tannennadelöl; Tea-tree-Öl; Terpentinöl; Thymianöl; Tolubalsam; Tonka-Absolue; Tuberosen-Absolue; Vanilleextrakt; Veilchenblätter-Absolue; Verbenaöl; Vetiveröl; Wacholderbeeröl; Weinhefenöl; Wermutöl; Wintergrünöl; Ylangöl; Ysopöl; Zibet-Absolue; Zimtblätteröl; Zimtrindenöl sowie Fraktionen davon, bzw. daraus isolierten Inhaltsstoffen;
• Einzel-Riechstoffe aus der Gruppe
• der Kohlenwasserstoffe, wie z.B. 3-Caren; alpha-Pinen; beta-Pinen; alpha-Terpinen; gamma-Terpinen; p-Cymol; Bisabolen; Camphen; Caryophyllen; Cedren; Farnesen; Limonen; Longifolen; Myrcen; Ocimen; Valencen; (E,Z)-1,3,5-Undecatrien; Styrol; Diphenylmethan;
• der aliphatischen Alkohole wie z.B. Hexanol; Octanol; 3-Octanol; 2,6-Dimethylheptanol; 2-Methyl-2-heptanol; 2-Methyl-2-octanol; (E)-2-Hexenol; (E)- und (Z)-3-Hexenol; 1-Octen-3-ol; Gemisch von 3,4,5,6,6-Pentamethyl-3/4-hepten-2-ol und 3,5,6,6-Tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-Nonadienol; 3,7-Dimethyl-7-methoxyoctan-2-ol; 9-Decenol; 10-Undecenol; 4-Methyl-3-decen-5-ol;
• der aliphatischen Aldehyde und deren Acetale wie z.B. Hexanal; Heptanal; Octanal; Nonanal; Decanal; Undecanal; Dodecanal; Tridecanal; 2-Methyloctanal; 2-Methylnonanal; (E)-2-Hexenal; (Z)-4-Heptenal; 2,6-Dimethyl-5-heptenal; 10-Undecenal; (E)-4-Decenal; 2-Dodecenal;2,6,10-Trimethyl-9-undecenal; 2,6,10-Trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-Dimethoxy-2,2,5-trimethyl-4-hexen; Citronellyloxyacetaldehyd; 1-(1-Methoxy-propoxy)-(E/Z)-3-hexen;
• der aliphatischen Ketone und deren Oxime wie z.B. 2-Heptanon; 2-Octanon; 3-Octanon; 2-Nonanon; 5-Methyl-3-heptanon; 5-Methyl-3-heptanonoxim; 2,4,4,7-Tetramethyl-6-octen-3-on; 6-Methyl-5-hepten-2-on;
• der aliphatischen schwefelhaltigen Verbindungen wie z.B. 3-Methylthio-hexanol; 3-Methylthiohexylacetat; 3-Mercaptohexanol; 3-Mercaptohexylacetat; 3-Mercaptohexylbutyrat; 3-Acetylthiohexylacetat; 1-Menthen-8-thiol;
• der aliphatischen Nitrile wie z.B. 2-Nonensäurenitril; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-Dimethyl-2,6-octadien-säurenitril; 3,7-Dimethyl-6-octensäurenitril;
• der Ester von aliphatischen Carbonsäuren wie z.B. (E)- und (Z)-3-Hexenylformiat; Ethylacetoacetat; Isoamylacetat; Hexylacetat; 3,5,5-Trimethylhexylacetat; 3-Methyl-2-butenyl-acetat; (E)-2-Hexenylacetat; (E)- und (Z)-3-Hexenylacetat; Octylacetat; 3-Octylacetat; 1-Octen-3-ylacetat; Ethylbutyrat; Butylbutyrat; Isoamylbutyrat; Hexylbutyrat; (E)- und (Z)-3-Hexenyl-isobutyrat; Hexylcrotonat; Ethylisovalerianat; Ethyl-2-methylpentanoat; Ethylhexanoat; Allylhexanoat; Ethylheptanoat; Allylheptanoat; Ethyloctanoat; Ethyl-(E,Z)-2,4-decadienoat; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoat;4-Methyl-2-pentyl-crotonat;
• der acyclischen Terpenalkohole wie z. B. Citronellol; Geraniol; Nerol; Linalool; Lavadulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6-Dimethyl-7-octen-2-ol; 2,6-Dimethyloctan-2-ol; 2-Methyl-6-methylen-7-octen-2-ol; 2,6-Dimethyl-5,7-octadien-2-ol; 2,6-Dimethyl-3,5-octadien-2-ol; 3,7-Dimethyl-4,6-octadien-3-ol; 3,7-Dimethyl-1,5,7-octatrien-3-ol 2,6-Dimethyl-2,5,7-octatrien-1-ol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate;
• der acyclischen Terpenaldehyde und ―ketone wie z. B. Geranial; Neral; Citronellal; 7-Hydroxy-3,7-dimethyloctanal; 7-Methoxy-3,7-dimethyloctanal; 2,6,10-Trimethyl-9-undecenal; Geranylaceton; sowie die Dimethyl- und Diethylacetale von Geranial, Neral, 7-Hydroxy-3,7-dimethyloctanal;
• der cyclischen Terpenalkohole wie z. B. Menthol; Isopulegol; alpha-Terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalooloxid; Nopol; Cedrol; Ambrinol; Vetiverol; Guajol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate;
• der cyclischen Terpenaldehyde und -ketone wie z. B. Menthon; Isomenthon; 8-Mercaptomenthan-3-on; Carvon; Campher; Fenchon; alpha-Ionon; beta-Ionon; alpha-n-Methylionon; beta-n-Methylionon; alpha-Isomethylionon; beta-Isomethylionon; alpha-Iron; alpha-Damascon; beta-Damascon; beta-Damascenon; delta-Damascon; gamma-Damascon; 1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-on; 1,3,4,6,7,8a-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-on;2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; Nootkaton; Dihydronootkaton; 4,6,8-Megastigmatrien-3-on; alpha-Sinensal; beta-Sinensal; acetyliertes Cedernholzöl (Methylcedrylketon);
• der cyclischen Alkohole wie z.B. 4-tert.-Butylcyclohexanol; 3,3,5-Trimethylcyclohexanol; 3-Isocamphylcyclohexanol; 2,6,9-Trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-Isobutyl-4-methyltetrahydro-2H-pyran-4-ol;
• der cycloaliphatischen Alkohole wie z.B. alpha,3,3-Trimethylcyclohexylmethanol;1-(4-Isopropylcyclohexyl)ethanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 2-Ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-(2,2,6-Trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-Trimethylcyclohexyl)hexan-3-ol;
• der cyclischen und cycloaliphatischen Ether wie z.B. Cineol; Cedrylmethylether; Cyclododecylmethylether;1,1-Dimethoxycyclododecan; (Ethoxymethoxy)cyclododecan; alpha-Cedrenepoxid; 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan; 3a-Ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-Trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-dien; Rosenoxid; 2-(2,4-Dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxan;
• der cyclischen und makrocyclischen Ketone wie z.B. 4-tert.-Butylcyclohexanon; 2,2,5-Trimethyl-5-pentylcyclopentanon; 2-Heptylcyclopentanon; 2-Pentylcyclopentanon; 2-Hydroxy-3-methyl-2-cyclopenten-1-on; 3-Methyl-cis-2-penten-1-yl-2-cyclopenten-1-on; 3-Methyl-2-pentyl-2-cyclopenten-1-on; 3-Methyl-4-cyclopentadecenon; 3-Methyl-5-cyclopentadecenon; 3-Methylcyclopentadecanon; 4-(1-Ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanon; 4-tert.-Pentylcyclohexanon; 5-Cyclohexadecen-1-on; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanon; 8-Cyclohexadecen-1-on; 9-Cycloheptadecen-1-on; Cyclopentadecanon; Cyclohexadecanon;
• der cycloaliphatischen Aldehyde wie z.B. 2,4-Dimethyl-3-cyclohexencarbaldehyd; 2-Methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexencarbaldehyd; 4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd;
• der cycloaliphatischen Ketone wie z. B. 1-(3,3-Dimethylcyclohexyl)-4-penten-1-on; 2,2-Dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanon; 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-on; 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert.-Butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keton;
• der Ester cyclischer Alkohole wie z.B. 2-tert-Butylcyclohexylacetat; 4-tert-Butylcyclohexylacetat; 2-tert-Pentylcyclohexylacetat; 4-tert-Pentylcyclohexylacetat; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthylacetat; 2-Cyclopentylcyclopentylcrotonat; 3-Pentyltetrahydro-2H-pyran-4-ylacetat; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylacetat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylpropionat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylisobutyrat; 4,7-Methanooctahydro-5, bzw. 6-indenylacetat;
• der Ester cycloaliphatischer Alkohole wie z.B.1-Cyclohexylethylcrotonat;
• der Ester cycloaliphatischer Carbonsäuren wie z. B. Allyl-3-cyclohexylpropionat; Allylcyclohexyloxyacetat; cis- und trans-Methyldihydrojasmonat; cis- und trans-Methyljasmonat; Methyl-2-hexyl-3-oxocyclopentancarboxylat; Ethyl-2-ethyl-6,6-dimethyl-2-cyclohexencarboxylat; Ethyl-2,3,6,6-tetramethyl-2-cyclohexencarboxylat; Ethyl-2-methyl-1,3-dioxolan-2-acetat;
• der araliphatischen Alkohole wie z. B. Benzylalkohol; 1-Phenylethylalkohol; 2-Phenylethylalkohol; 3-Phenylpropanol; 2-Phenylpropanol; 2-Phenoxyethanol; 2,2-Dimethyl-3-phenylpropanol; 2,2-Dimethyl-3-(3-methylphenyl)propanol; 1,1-Dimethyl-2-phenylethylalkohol; 1,1-Dimethyl-3-phenylpropanol; 1-Ethyl-1-methyl-3-phenylpropanol; 2-Methyl-5-phenylpentanol; 3-Methyl-5-phenylpentanol; 3-Phenyl-2-propen-1-ol; 4-Methoxybenzylalkohol; 1-(4-Isopropylphenyl)ethanol;
• der Ester von araliphatischen Alkoholen und aliphatischen Carbonsäuren wie z.B. Benzylacetat; Benzylpropionat; Benzylisobutyrat; Benzylisovalerianat; 2-Phenylethylacetat; 2-Phenylethylpropionat; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-Phenylethylacetat; alpha-Trichlormethylbenzylacetat; alpha,alpha-Dimethylphenylethylacetat; alpha,alpha-Dimethylphenylethylbutyrat; Cinnamylacetat; 2-Phenoxyethylisobutyrat; 4-Methoxybenzylacetat;
• der araliphatischen Ether wie z.B. 2-Phenylethylmethylether; 2-Phenylethylisoamylether; 2-Phenylethyl-1-ethoxyethylether; Phenylacetaldehyddimethylacetal; Phenylacetaldehyddiethylacetal; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-Trimethyl-4-phenyl-1,3-dioxan; 4,4a,5,9b-Tetrahydroindeno[1,2-d]-m-dioxin; 4,4a,5,9b-Tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;
• der aromatischen und araliphatischen Aldehyde wie z. B. Benzaldehyd; Phenylacetaldehyd; 3-Phenylpropanal; Hydratropaaldehyd; 4-Methylbenzaldehyd; 4-Methylphenylacetaldehyd; 3-(4-Ethylphenyl)-2,2-dimethylpropanal; 2-Methyl-3-(4-isopropylphenyl)propanal; 2-Methyl-3-(4-tert.-butylphenyl)propanal; 2-Methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert.-Butylphenyl)propanal; Zimtaldehyd; alpha-Butylzimtaldehyd; alpha-Amylzimtaldehyd; alpha-Hexylzimtaldehyd; 3-Methyl-5-phenylpentanal; 4-Methoxybenzaldehyd; 4-Hydroxy-3-methoxybenzaldehyd; 4-Hydroxy-3-ethoxybenzaldehyd; 3,4-Methylendioxybenzaldehyd; 3,4-Dimethoxybenzaldehyd; 2-Methyl-3-(4-methoxyphenyl)propanal; 2-Methyl-3-(4-methylendioxyphenyl)propanal;
• der aromatischen und araliphatischen Ketone wie z.B. Acetophenon; 4-Methylacetophenon; 4-Methoxyacetophenon; 4-tert.-Butyl-2,6-dimethylacetophenon; 4-Phenyl-2-butanon; 4-(4-Hydroxyphenyl)-2-butanon; 1-(2-Naphthalenyl)ethanon;2-Benzofuranylethanon;(3-Methyl-2-benzofuranyl)ethanon; Benzophenon; 1,1,2,3,3,6-Hexamethyl-5-indanylmethylketon; 6-tert.-Butyl-1,1-dimethyl-4-indanylmethylketon; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanon; 5',6',7',8'-Tetrahydro-3',5',5',6',8',8'-hexamethyl-2-acetonaphthon;
• der aromatischen und araliphatischen Carbonsäuren und deren Ester wie z.B. Benzoesäure; Phenylessigsäure; Methylbenzoat; Ethylbenzoat; Hexylbenzoat; Benzyl-benzoat; Methylphenylacetat; Ethylphenylacetat; Geranylphenylacetat; Phenylethyl-phenylacetat; Methylcinnmat; Ethylcinnamat; Benzylcinnamat; Phenylethylcinnamat; Cinnamylcinnamat; Allylphenoxyacetat; Methylsalicylat; Isoamylsalicylat; Hexylsalicylat; Cyclohexylsalicylat; Cis-3-Hexenylsalicylat; Benzylsalicylat; Phenylethylsalicylat; Methyl-2,4-dihydroxy-3,6-dimethylbenzoat; Ethyl-3-phenylglycidat; Ethyl-3-methyl-3-phenylglycidat;
• der stickstoffhaltigen aromatischen Verbindungen wie z.B. 2,4,6-Trinitro-1,3-dimethyl-5-tert.-butylbenzol; 3,5-Dinitro-2,6-dimethyl-4-tert.-butylacetophenon; Zimtsäurenitril; 3-Methyl-5-phenyl-2-pentensäurenitril; 3-Methyl-5-phenylpentansäurenitril; Methylanthranilat; Methy-N-methylanthranilat; Schiff'sche Basen von Methylanthranilat mit 7-Hydroxy-3,7-dimethyloctanal, 2-Methyl-3-(4-tert.-butylphenyl)propanal oder 2,4-Dimethyl-3-cyclohexencarbaldehyd; 6-Isopropylchinolin; 6-Isobutylchinolin; 6-sec.-Butylchinolin;2-(3-Phenylpropyl)pyridin; Indol; Skatol;
• der Phenole, Phenylether und Phenylester wie z.B. Estragol; Anethol; Eugenol; Eugenylmethylether; Isoeugenol; Isoeugenylmethylether; Thymol; Carvacrol; Diphenylether; beta-Naphthylmethylether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-Dimethoxybenzol; Eugenylacetat; 2-Methoxy-4-methylphenol; 2-Ethoxy-5-(1-propenyl)phenol; p-Kresylphenylacetat;
• der heterocyclischen Verbindungen wie z.B. 2,5-Dimethyl-4-hydroxy-2H-furan-3-on; 2-Ethyl-4-hydroxy-5-methyl-2H-furan-3-on; 3-Hydroxy-2-methyl-4H-pyran-4-on; 2-Ethyl-3-hydroxy-4H-pyran-4-on;
• der Lactone wie z.B. 1,4-Octanolid; 3-Methyl-1,4-octanolid; 1,4-Nonanolid; 1,4-Decanolid; 8-Decen-1,4-olid; 1,4-Undecanolid; 1,4-Dodecanolid; 1,5-Decanolid; 1,5-Dodecanolid;4-Methyl-1,4-decanolid; 1,15-Pentadecanolid; cis- und trans-11-Pentadecen-1,15-olid; cis-und trans-12-Pentadecen-1,15-olid; 1,16-Hexadecanolid; 9-Hexadecen-1,16-olid; 10-Oxa-1,16-hexadecanolid; 11-Oxa-1,16-hexadecanolid; 12-Oxa-1,16-hexadecanolid;

Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balms, tinctures such. B.

• ambergris tincture; Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Buccoblätteröl; Cabreuvaöl; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Castoreum absolute; Cedernblätteröl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak moss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyptus oil; Fennel oil; Pine needle oil; galbanum; Galbanumresin; geranium; Grapefruit oil; guaiac wood; gurjun balsam; gurjun balsam oil; Helichrysum absolute; Helichrysumöl; Ginger oil; Iris root absolute; Orris root oil; Jasmine absolute; calamus; Chamomile oil blue; Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; labdanum; Labdanum absolute; Labdanumresin; Lavandin absolute; lavender oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Lime oil pressed; linaloe; Litseacubeba oil; Bay leaf oil; Macisöl; Marjoram oil; Mandarin oil; Massoirindenöl; Mimosa absolute; Musk seed oil; musk tincture; Clary sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; myrtle; Clove leaf oil; Clove flower oil; neroli; Olibanum absolute; olibanum; Opopanaxöl; Orange blossom absolute; Orange oil; oregano; Palmarosa oil; patchouli oil; perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil; chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Sage oil Dalmatian; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree oil; turpentine; Thyme oil; Tolu; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; verbena; vetiver; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; ylang oil; hyssop oil; Civet absolute; cinnamon leaf; Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;
• Single fragrances from the group
• hydrocarbons, such as 3-carene; alpha-pinene; beta-pinene; alpha-terpinene; gamma-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1,3,5-undecatriene; styrene; diphenylmethane;
• the aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-octene-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-Nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
• the aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methyl nonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; (1-methoxy-propoxy) 1- - 3-ene (E / Z);
• the aliphatic ketones and their oximes such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
• the aliphatic sulfur-containing compounds such as 3-methylthio-hexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
• the aliphatic nitriles such as 2-nonenitrile; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-dimethyl-2,6-octadiene-acid nitrile; 3,7-dimethyl-6-octensäurenitril;
• the ester of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethylisovalerianat; Ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; Ethyl (E, Z) -2,4-decadienoate; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl-crotonate;
• the acyclic terpene alcohols such. Citronellol; geraniol; nerol; linalool; Lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadiene-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
• the acyclic terpene aldehydes and ketones such. B. Geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;
• the cyclic terpene alcohols such. Menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; soborneol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
• the cyclic terpene aldehydes and ketones such. Eg menthone; menthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-irone; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma-damascone; 1- (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; nootkatone; Dihydronootkaton; 4,6,8-Mega stigma triene-3-one; alpha-sinensal; beta-sinensal; acetylated cedarwood oil (methyl cedryl ketone);
• the cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
• the cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-Dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2,6-trimethylcyclohexyl) hexan-3-ol;
• the cyclic and cycloaliphatic ethers such as cineole; cedryl methyl ether; Cyclododecyl; 1,1-Dimethoxycyclododecan; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6,6,9a-tetramethyl-dodecahydronaphtho [2,1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1,5,9-trimethyl-13-oxabicyclo [10.1.0] trideca-4,8-diene; rose oxide; 2- (2,4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;
• the cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanon; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;
• the cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexene carbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;
• the cycloaliphatic ketones such. B. 1- (3,3-dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1- (2,4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1- (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
• the ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthyl acetate; 2-Cyclopentylcyclopentylcrotonat; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl acetate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenylpropionate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl isobutyrate, respectively; 4,7-Methanooctahydro-5, or 6-indenyl acetate;
• the ester of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate;
• the esters of cycloaliphatic carboxylic acids such as. For example, allyl-3-cyclohexylpropionate; Allylcyclohexyloxyacetat; cis- and trans-methyldihydrojasmonate; cis- and trans-methyl jasmonate; Methyl-2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Ethyl-2-methyl-1,3-dioxolan-2-acetate;
• the araliphatic alcohols such. B. benzyl alcohol; 1-phenylethyl; 2-phenylethyl; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl; 1- (4-isopropylphenyl) ethanol;
• the ester of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-Dimethylphenylethylacetat; alpha, alpha-Dimethylphenylethylbutyrat; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
• the araliphatic ethers such as 2-phenylethyl methyl ether; 2-Phenylethylisoamylether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde; phenylacetaldehyde; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;
• the aromatic and araliphatic aldehydes such. B. benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyd; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; propanal, 2-methyl-3- (4-tert-butylphenyl); 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-Butylzimtaldehyd; alpha-amyl cinnamic aldehyde; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-Hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;
• the aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; 2-Benzofuranylethanon; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone; 1- [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 8'-hexamethyl-2-acetonaphthone, 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ', 8';
• the aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Ethyl-3-methyl-3-phenylglycidate;
• the nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone; cinnamic acid; 3-methyl-5-phenyl-2-pentensäurenitril; 3-methyl-5-phenylpentansäurenitril; methyl anthranilate; Methyl N-methylanthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexene carbaldehyde; 6-Isopropyl; 6-Isobutylchinolin; 6-sec.-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatol;
• the phenols, phenyl ethers and phenyl esters such as estragole; anethole; eugenol; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methyl phenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
• heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
• the lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide, 4-methyl-1,4-decanolide; 1.15 pentadecanolide; cis- and trans-11-pentadecene-1,15-olide; cis- and trans-12-pentadecene-1,15-olide; 1,16-hexadecanolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide;

Ethylene-1,12-dodecanedioate; Ethylene-1,13-tridecandioat; coumarin; 2,3-dihydrocoumarin; Octahydrocoumarin.

a) Bu₂NH; b) kat. NaOH, ROH; H₂SO₄ As will be explained in more detail below (compare Synthesis path according to Scheme 1 and Example 1), the compound of formula (I) can be synthesized in a particularly economical manner.

a) Bu ₂ NH; b) cat. NaOH, ROH; H ₂ SO ₄

Starting from alpha, beta-unsaturated ketones or aldehydes of the general formula (IV) and 1,3-dicarbonyl compounds of the general formula (V), compounds of the general formula (I) are prepared by a base-catalyzed cyclization reaction with subsequent saponification and decarboxylation. Unavailable compounds of the general formula (IV) can be prepared by base-catalyzed aldol condensation from compounds of the general formulas (II) and (III). Wherein the meaning of the radicals R1, R2, R3, R4, R5 and R6 in the compounds of the formula (II), (III), (IV) and (V) are each the same as the meaning of the identically named radicals of the compound of Formula (I).

As described above, in the context of the present invention, new compounds of the formula (I) and corresponding mixtures thereof are also given. The preparation of these novel compounds of formula (I) (as described above) by means of a method according to the invention.

• (i) Bereitstellen oder Herstellen einer Verbindung der Formel (IV)
  
  vorzugsweise durch Umsetzen einer Verbindung der Formel (II) und einer Verbindung der Formel (III), so dass eine Verbindung der Formel (IV) resultiert,
  
  sowie
• (ii) Umsetzen der Verbindung der Formel (IV) und einer Verbindung der Formel (V),
  
  so dass eine Verbindung der Formel (I) resultiert,

wobei die Bedeutung der Reste R1, R2, R3, R4, R5 und R6 in den Verbindungen der Formel (II), (III), (IV) und (V) jeweils die gleiche ist wie die Bedeutung der gleich bezeichneten Reste der Verbindung der Formel (I).Accordingly, the present invention also relates to a process for the preparation of these novel compounds of the formula (I), comprising the following steps:

• (i) providing or preparing a compound of the formula (IV)
  
  preferably by reacting a compound of formula (II) and a compound of formula (III) to give a compound of formula (IV),
  
  such as
• (ii) reacting the compound of the formula (IV) and a compound of the formula (V),
  
  such that a compound of formula (I) results,

wherein the meaning of the radicals R1, R2, R3, R4, R5 and R6 in the compounds of the formula (II), (III), (IV) and (V) are each the same as the meaning of the identically designated radicals of the compound of Formula (I).

According to the invention, preference is given to a process for the preparation of the novel compounds of the formula (I) in which an alkali metal hydroxide, an alkaline earth hydroxide and / or an alcoholate, preferably at least sodium hydroxide or potassium hydroxide, is used as catalyst in step (ii).

Also preferred according to the invention is a process for the preparation of the novel compounds of the formula (I), in which the reaction in step (ii) is carried out in a solvent, preferably in a polar solvent, more preferably in a polar protic solvent, most preferably in an alcohol is carried out. Particularly preferred according to the invention is a process for the preparation of the novel compounds of the formula (I), in which the reaction of the compound of the formula (II) with the compound of the formula (III) in step (ii) is carried out in the presence of a secondary amine, preferably selected from the group consisting of piperidine, dibutylamine, diethylamine and dimethylamine
and or
the reaction of the compound of the formula (II) with the compound of the formula (III) in step (ii) is carried out in the presence of water as solvent.

a) Piperidin, NaOHAlternatively, z. B. the compounds of the invention 13, 43, 44 and 45 (synthesis route Scheme 2 and Example 22), the formula (VIII) are synthesized in a particularly simple manner.

a) piperidine, NaOH

The compounds of the general formula (VIII) are prepared starting from aldehydes of the general formula (VI) and 1,3-dicarbonyl compounds of the formula (VII) by a base-catalyzed cyclization reaction with subsequent saponification and decarboxylation. The radical R4 of the formula (VIII) has the meaning: methyl, ethyl, n-propyl and isopropyl.

• (i) Bereitstellen oder Herstellen einer Verbindung der Formel (VI)
  wobei die Bedeutung des Restes R4 die gleiche ist wie die Bedeutung des gleich bezeichneten Restes der Verbindung der Formel (I),
  sowie
• (ii) Umsetzen der Verbindung der Formel (VI) und einer Verbindung der Formel (VIII),
  

wobei der Rest R ein verzweigter oder unverzweigter, gesättigter oder ungesättigter Kohlenwasserstoffrest ist, vorzugsweise Methyl, Ethyl, Propyl, Butyl ist,
so dass eine Verbindung der Formel (I) resultiert,
und wobei vorzugsweise als Katalysator in Schritt (ii) ein Alkalihydroxid, ein Erdalkalihydroxid und/oder ein Alkoholat, vorzugsweise zumindest Natriumhydroxid oder Kaliumhydroxid verwendet wird
und wobei vorzugsweise das Umsetzen der Verbindung der Formel (VI) mit der Verbindung der Formel (VII) in Schritt (ii) in Gegenwart eines sekundären Amins erfolgt, vorzugsweise ausgewählt aus der Gruppe bestehend aus Piperidin, Dibutylamin, Dietylamin und Dimethylamin erfolgt.Accordingly, the present invention also relates to an alternative process for preparing a compound of the formula (I), preferably one of the compounds 43, 44 or 45 as defined above,
where the radicals of the compound of the formula (I) are those
R1 means methyl
R2 ethyl means
R3 is hydrogen,
R 4 is methyl, ethyl, n-propyl or isopropyl,
R5 is hydrogen,
R6 is hydrogen,
with the following steps:

• (i) providing or preparing a compound of formula (VI)
  wherein the meaning of the radical R4 is the same as the meaning of the same named radical of the compound of the formula (I),
  such as
• (ii) reacting the compound of the formula (VI) and a compound of the formula (VIII),
  

wherein the radical R is a branched or unbranched, saturated or unsaturated hydrocarbon radical, preferably methyl, ethyl, propyl, butyl,
such that a compound of formula (I) results,
and wherein preferably as the catalyst in step (ii) an alkali hydroxide, an alkaline earth hydroxide and / or an alcoholate, preferably at least sodium hydroxide or potassium hydroxide is used
and wherein preferably the reaction of the compound of the formula (VI) with the compound of the formula (VII) in step (ii) takes place in the presence of a secondary amine, preferably selected from the group consisting of piperidine, dibutylamine, diethylamine and dimethylamine.

Hereinafter, the present invention will be explained in more detail by way of examples. Unless otherwise indicated, all figures are by weight.

Example 1: Synthesis of 6-ethyl-4-isopropylcyclohex-2-en-1-one (1) Example 1.1: Synthesis of 3-methyl-2-methylene-butanal

To a solution of isovaleraldehyde (206.7 g, 2.4 mol) and 37% aqueous formaldehyde solution (200.6 g, 2.5 mol) is added dropwise at 80 ° C dibutylamine (9.3 g, 70 mmol). Subsequently, the reaction mixture is refluxed for 2.5 hours. For workup, the reaction solution is cooled to room temperature and the phases are separated. Obtained is 3-methyl-2-methylenebutanal in the form of a colorless oil (240 g, 96%).

¹ H-NMR _(CDCl3, 400 MHz): δ 9:54 (s, 1H), 6.25 (m, 1H), 5.95 (s, 1H), 2.80 (m, 1H), 1.08 ppm (d, J = 7Hz, 6H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 194.7, 156.5, 132.2, 26.2, 21.4 ppm. MS (EI): m / z = 27 (38), 41 (100), 55 (60), 69 (59), 83 (28), 98 (39, M ⁺ ).

Example 1.2: Synthesis of 6-ethyl-4-isopropylcyclohex-2-en-1-one (1)

To a 50% aqueous NaOH (8.8 g, 0.11 mol) in ethanol (90 mL) was added ethyl 2-ethylacetoacetate (17.5 g, 0.11 mol) in ethanol (25 mL) followed by 3-methyl-2-methylenebutanal (10.3 g, 0.11 mol) in ethanol (25 mL) at 0 ° C. The reaction mixture is refluxed for 1 hour and then the solvent is distilled off. The reaction mixture is treated with water (170 mL) and MtBE (150 mL) and the phases are separated. The organic phase is neutralized with 50% aqueous sulfuric acid (8.8 g), dried over sodium sulfate and concentrated in vacuo. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 40/1) gives 6-ethyl-4-isopropylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (2.8 g, 17%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.81 (m, 1H) 6.00 (m, 1H), 2:39 (m, 1H), 2.17 (m, 1H), 2:00 (m, 1H), 1.94 (m, 1H), 1.82 (m, 1H), 1.45 (m, 1H), 1.39 (m, 1H), 0.96 (d, J = 7Hz, 3H), 0.95 (d, J = 7Hz, 3H), 0.94 ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 201.8, 152.9, 129.9, 47.8, 43.4, 31.7, 30.6, 22.0, 19.3, 19.2, 11.1 ppm. MS (EI): m / z = 27 (9), 41 (19), 55 (11), 67 (14), 81 (12), 95 (100), 110 (7), 123 (12), 138 (15), 151 (2), 166 (3, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.84 (m, 1H), 5.93 (m, 1H), 2.30 (m, 2H), 1.90 (m, 2H), 1.82 (m, 1H), 1.72 (m, 1H), 1.50 (m, 1H), 1.00 (d, J = 7Hz, 6H), 0.94ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.9, 152.9, 128.5, 46.7, 38.9, 31.4, 29.1, 23.1, 19.9, 11.9 ppm. MS (EI): m / z = 27 (4), 41 (11), 55 (8), 67 (10), 81 (9), 95 (100), 110 (8), 123 (8), 138 (15), 151 (4), 166 (8, M ⁺ ).

Odor description of 6-ethyl-4-isopropylcyclohex-2-en-1-one: green, fruity, grapefruit, rhubarb, citrus, fresh, floral.

Example 2 : Synthesis of 4-isopropyl-6-methylcyclohex-2-en-1-one (2)

Synthesis analogous to Example 1.2, starting from 2-methylacetessigsäureethylester and 3-methyl-2-methylenbutanal. Fractional distillation gives 4-isopropyl-6-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (34%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.82 (m, 1H) 6.00 (m, 1H), 2:42 (m, 1H), 2:35 (m, 1H), 1.97 (m, 1H), 1.80 (m, 1H), 1.49 (m, 1H), 1.14 (d, J = 7Hz, 3H), 0.96 (d, J = 7Hz, 3H), 0.94ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.4, 153.3, 129.5, 43.4, 41.6, 34.1, 31.6, 19.4, 19.1, 15.1 ppm. MS (EI): m / z = 27 (13), 43 (23), 55 (9), 67 (17), 82 (21), 95 (100), 110 (42), 137 (4), 152 (15, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.89 (m, 1H), 5.95 (m, 1H), 2.30 (m, 1H), 1.98 (m, 1H), 1.81 (m, 2H), 1.15 (d, J = 7Hz, 3H), 1.00ppm (d, J = 7Hz, 6H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 203.0, 153.1, 128.3, 39.3, 39.2, 32.2, 31.4, 20.3, 20.1, 15.8 ppm. MS (EI): m / z = 27 (11), 43 (26), 55 (9), 67 (17), 82 (17), 95 (100), 110 (41), 137 (3), 152 (13, M ⁺ ).

Odor description of 4-isopropyl-6-methylcyclohex-2-en-1-one: fresh, sweet, spicy, aromatic, fruity, grapefruit, vermouth tea.

Description of taste of 4-isopropyl-6-methylcyclohex-2-en-1-one: herbaceous, sage, balsamic, spearmint, cooling.

Example 3: Synthesis of 4-isopropyl-2-methylcyclohex-2-en-1-one (3)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and 3-methyl-2-methylenebutanal. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 40/1 to 30/1) gives 4-isopropyl-2-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (17%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6.65 (m, 1H), 2:53 (m, 1H), 2:32 (m, 1 H), 2.27 (m, 1H), 1.97 (m, 1H), 1.78 (m, 3H), 1.76 (m, 1H), 1.72 (m, 1H), 0.96 (d, J = 7Hz, 3H), 0.94ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.4, 149.5, 135.5, 42.9, 37.7, 31.8, 25.7, 19.7, 19.4, 16.1 ppm. MS (EI): m / z = 27 (18), 41 (46), 53 (19), 67 (23), 81 (46), 95 (100), 110 (79), 123 (4), 137 (8), 152 (44, M ⁺ ).

Odor description of 4-isopropyl-2-methylcyclohex-2-en-1-one: spicy, herbaceous, greasy, floral, cumin.

Example 4: Synthesis of 2-ethyl-4-isopropylcyclohex-2-en-1-one (4)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 3-methyl-2-methylenebutanal. Column chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate 25/1) gives 2-ethyl-4-isopropylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (23%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6.60 (m, 1H), 2:52 (m, 1H), 2:32 (m, 1H), 2.28 (m, 1H), 2.21 (m, 1H), 1.96 ( m, 1H), 1.80 (m, 1H), 1.70 (m, 1H), 1.01 (t, J = 7Hz, 3H), 0.97 (d, J = 7Hz, 3H), 0.95ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.9, 147.9, 141.0, 42.7, 37.9, 31.8, 25.4, 22.6, 19.7, 19.4, 13.1 ppm. MS (EI): m / z = 27 (49), 41 (93), 55 (52), 67 (56), 81 (100), 95 (96), 109 (83), 123 (61), 137 (7), 151 (9), 166 (39, M ⁺ ).

Odor description of 2-ethyl-4-isopropylcyclohex-2-en-1-one: fruity, damascone, saffron, spicy, chamomile.

Description of the taste of 2-ethyl-4-isopropylcyclohex-2-en-1-one: herbaceous, pepper, geranium, woody, flowery.

Example 5 : Synthesis of 5-ethyl-4-methylcyclohex-2-en-1-one (5)

Synthesis analogous to Example 1.2, starting from ethyl acetoacetate and 2-methyl-2-pentenal. Fractional distillation gives 5-ethyl-4-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (10%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.74 (m, 1H), 5.94 (m, 1H), 2:55 (m, 1H), 2.28 (m, 1H), 2.14 (m, 1H), 1.70 (m, 1H), 1.64 (m, 1H), 1.35 (m, 1H), 1.18 (d, J = 7Hz, 3H), 0.91ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.4, 156.2, 128.3, 43.1, 41.7, 35.9, 25.7, 18.5, 10.5 ppm. MS (EI): m / z = 27 (25), 39 (34), 54 (45), 68 (42), 82 (100), 95 (13), 109 (19), 123 (4), 138 (26, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.96 (m, 1H), 5.94 (m, 1H), 2:55 (m, 1H), 2:35 (m, 2H), 2:06 (m, 1H), 1.43 (m, 2H), 1.02 (d, J = 7Hz, 3H), 0.93ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.1, 156.1, 128.1, 39.5, 39.2, 33.0, 24.9, 12.0, 11.3 ppm. MS (EI): m / z = 27 (19), 39 (28), 54 (40), 68 (9), 82 (100), 95 (9), 109 (15), 123 (2), 138 (19, M ⁺ ).

Odor description of 5-ethyl-4-methylcyclohex-2-en-1-one: spicy, almond.

Example 6 : Synthesis of 5-ethyl-2,4-dimethylcyclohex-2-en-1-one (8)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and 2-methyl-2-pentenal. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 20/1) gives 5-ethyl-2,4-dimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (5%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:48 (m, 1H), 2:56 (m, 1H), 2.25 (m, 1H), 2.11, (m, 1H), 1.75 (m, 3H), 1.64 (m, 2H), 1.26 (m, 1H), 1.14 (d, J = 7Hz, 3H), 0.91ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.5, 151.5, 134.2, 43.6, 42.0, 36.2, 25.7, 18.8, 15.6, 10.6 ppm. MS (EI): m / z = 27 (15), 41 (45), 55 (21), 69 (60), 82 (14), 95 (100), 109 (9), 123 (18), 137 (2), 152 (11, M ⁺ ).

Nebenverbindung : ¹ H-NMR (CDCl3 _, 400 MHz): δ 6.70 (m, 1H), 2.50 (m, 1H), 2.30 (m, 2H), 2.04 (m, 1H), 1.75 (m, 3H), 1.35 (m, 2H), 0.99 (d, J = 7Hz, 3H), 0.90ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.2, 151.3, 133.9, 39.6, 33.2, 24.9, 15.8, 12.3, 11.3 ppm. MS (EI): m / z = 27 (17), 41 (42), 55 (25), 69 (58), 82 (8), 95 (100), 109 (17), 123 (33), 137 (2), 152 (17, M ⁺ ).

Odor description of 5-ethyl-2,4-dimethylcyclohex-2-en-1-one: aromatic, herbaceous, spicy, medicinal, almond, coumarin.

Example 7 : Synthesis of 2,5-diethyl-4-methylcyclohex-2-en-1-one (9)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 2-methyl-2-pentenal. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 99/1) gives 2,5-diethyl-4-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (10%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:42 (m, 1H), 2.86 (m, 1H), 2:30 to 2:15 (m, 4H), 1.64 (m, 2H), 1.30 (m, 1H ), 1.15 (d, J = 7Hz, 3H), 1.00 (t, J = 7Hz, 3H), 0.99ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.2, 149.9, 139.7, 43.4, 42.3, 36.1, 25.7, 22.1, 18.9, 12.9, 10.6 ppm. MS (EI): m / z = 29 (15), 41 (41), 55 (51), 67 (79), 83 (74), 95 (50), 109 (100), 124 (11), 137 (75), 151 (8), 166 (30, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.65 (m, 1H), 2:55 (m, 1H), 2:35 to 2:15 (m, 4H), 2:02 (m, 1H), 1:37 (m, 2H ), 1.00 (t, J = 7Hz, 3H), 0.99 (d, J = 7Hz, 3H), 0.92ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.8, 149.7, 139.4, 39.8, 39.4, 33.1, 24.8, 22.2, 12.9, 12.4, 11.3 ppm. MS (EI): m / z = 29 (15), 41 (42), 55 (48), 67 (93), 83 (67), 95 (55), 109 (100), 124 (15), 137 (71), 151 (8), 166 (27, M ⁺ ).

Odor description of 2,5-diethyl-4-methylcyclohex-2-en-1-one: spicy, aromatic, spearmint, saffron, anise, fennel, tobacco.

Example 8 : Synthesis of 3-ethyl-5-methylcyclohex-2-en-1-one (10)

Synthesis analogous to Example 1.2, starting from ethyl acetoacetate and 4-hexen-3-one. Fractional distillation gives 3-ethyl-5-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (55%).

¹ H-NMR _(CDCl3, 400 MHz): δ 5.87 (m, 1H), 2:43 (m, 1H), 2.31 (m, 1H), 2.24 (m, 2H), 2.17 (m, 1H), 2:04 ( m, 1H), 2.03 (m, 1H), 1.10 (t, J = 7Hz, 3H), 1.07 ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.3, 167.0, 124.3, 45.6, 38.2, 30.8, 30.2, 21.2, 11.3 ppm. MS (EI): m / z = 39 (19), 53 (15), 67 (30), 81 (37), 96 (100), 109 (2), 123 (6), 138 (42, M ⁺ ).

Odor description of 3-ethyl-5-methylcyclohex-2-en-1-one: spicy, aromatic, lovage, celery, fenugreek.

Example 9 : Synthesis of 3-ethyl-5,6-dimethylcyclohex-2-en-1-one (12)

Synthesis analogous to Example 1.2, starting from 2-methylacetessigsäureethylester and 4-hexen-3-one. Fractional distillation gives 3-ethyl-5,6-dimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (12%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 5.85 (m, 1H), 2.30 (m, 1H), 2.21 (m, 2H), 2.10 (m, 1H). 1.99 (m, 1H), 1.84 (m, 1H), 1.15 (d, J = 7Hz, 3H), 1.09 (t, J = 7Hz, 3H), 1.08ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 201.2, 165.3, 123.8, 47.8, 38.2, 36.2, 30.6, 20.0, 12.4, 11.3 ppm. MS (EI): m / z = 27 (11), 39 (17), 53 (13), 67 (26), 81 (32), 96 (100), 109 (4), 123 (4), 137 (9), 152 (11, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 5.81 (m, 1H), 2:43 (m, 1H), 2.30 (m, 2H), 2.21 (m, 2H), 2.10 (m, 1H), 1.12 (t, J = 7Hz, 3H), 1.04 (d, J = 7Hz, 3H), 0.95ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 203.5, 165.1, 123.3, 45.5, 35.8, 33.3, 30.7, 15.7, 11.3, 10.8 ppm. MS (EI): m / z = 27 (11), 39 (17), 53 (13), 67 (26), 81 (32), 96 (100), 109 (2), 123 (4), 137 (9), 152 (13, M ⁺ ).

Odor description of 5-ethyl-5,6-dimethylcyclohex-2-en-1-one: spicy, saffron, green, natural, mint.

Example 10: Synthesis of 3-ethyl-2,5-dimethylcyclohex-2-en-1-one (13)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and 4-hexen-3-one. Fractional distillation gives 3-ethyl-2,5-dimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (31%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2:47 (m, 1H), 2:36 (m, 1H), 2.23 (m, 2H), 2.10 (m, 1H), 2:08 (m, 1H), 2:03 ( m, 1H), 1.76 (m, 3H), 1.07 (t, J = 7Hz, 3H), 1.04 ppm (m, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.8, 159.5, 129.8, 45.8, 38.7, 29.8, 28.2, 21.2, 11.6, 10.2 ppm.

MS (EI): m / z = 27 (19), 41 (42), 53 (22), 67 (100), 82 (27), 95 (32), 110 (90), 123 (10), 137 (27), 152 (68, M ⁺ ).

Odor description of 3-ethyl-2,5-dimethylcyclohex-2-en-1-one: spicy, woody, leather, saffron, green, soft, creamy.

Taste description of 3-ethyl-2,5-dimethylcyclohex-2-en-1-one: medicinal, fresh, woody.

Example 11: Synthesis of 2,3-diethyl-5-methylcyclohex-2-en-1-one (14)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 4-hexen-3-one. Fractional distillation gives 2,3-diethyl-5-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (40%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2.64 (m, 1H), 2:34 (m, 1H), 2.27 (m, 4H), 2:08 (m, 3H), 1:09 (t, J = 8 Hz, 3H ), 1.03 (d, J = 6Hz, 3H), 0.92ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.5, 159.1, 136.0, 46.2, 38.5, 29.8, 27.7, 21.2, 18.1, 14.2, 12.4 ppm. MS (EI): m / z = 29 (11), 41 (44), 55 (21), 67 (32), 81 (100), 95 (32), 109 (47), 124 (93), 137 (46), 151 (30), 166 (100, M ⁺ ).

Odor description of 2,3-diethyl-5-methylcyclohex-2-en-1-one: spicy, herbaceous, saffron.

Example 12: Synthesis of 4,5-dimethylcyclohex-2-en-1-one (15)

Synthesis analogous to Example 1.2, starting from ethyl acetoacetate and tiglic aldehyde. Fractional distillation gives 4,5-dimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (15%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.74 (m, 1H), 5.91 (m, 1H) 2.46 (m, 1H), 2.17 (m, 1H), 2.15 (m, 1H), 1.83 (m, 1H), 1.18 (d, J = 7Hz, 3H), 1.08ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.3, 156.2, 128.5, 45.6, 38.3, 37.1, 19.6, 18.5 ppm. MS (EI): m / z = 27 (27), 39 (40), 54 (53), 68 (61), 82 (100), 96 (19), 109 (10), 124 (41, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:56 (m, 1H), 5.94 (m, 1H), 2:55 (m, 1H), 2:34 (m, 3H), 1:06 (d, J = 7Hz , 3H), 0.99 ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.6, 155.4, 128.1, 42.7, 34.7, 32.7, 16.6, 13.4 ppm. MS (EI): m / z = 27 (23), 39 (33), 54 (48), 68 (27), 82 (100), 96 (19), 109 (10), 124 (30, M ⁺ ).

Odor description of 4,5-dimethylcyclohex-2-en-1-one: almond, sweet, tobacco, cherry, fruity, coumarin.

Example 13: Synthesis of 2,4,5-trimethylcyclohex-2-en-1-one (18)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and Tiglinaldehyd. Fractional distillation gives 2,4,5-trimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (30%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:48 (m, 1H), 2:45 (m, 1H), 2.14 (m, 1H), 2.12 (m, 1H), 1.79 (m, 1H), 1.76 (m, 3H), 1.14 (d, J = 7Hz, 3H), 1.05ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.5, 151.5, 134.4, 45.8, 38.6, 37.5, 19.5, 18.8, 15.6 ppm. MS (EI): m / z = 27 (19), 41 (56), 53 (28), 69 (100), 81 (48), 95 (92), 110 (42), 123 (15), 138 (33, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.60 (m, 1H), 2:53 (m, 1H), 2:33 (m, 3H), 1.76 (m, 3H), 1:03 (d, J = 7Hz , 3H), 0.95 ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.1, 150.6, 133.9, 42.8, 37.1, 34.1, 16.5, 15.7, 13.8 ppm. MS (EI): m / z = 27 (22), 41 (60), 53 (31), 69 (100), 81 (59), 95 (100), 110 (47), 123 (15), 138 (31, M ⁺ ).

Odor description of 2,4,5-trimethylcyclohex-2-en-1-one: spicy, aromatic, cherry, coumarin, almond.

Example 14: Synthesis of 2-ethyl-4,5-dimethylcyclohex-2-en-1-one (19)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and Tiglinaldehyd. Fractional distillation gives 2-ethyl-4,5-dimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (29%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:42 (m, 1H) 2.46 (m, 1H), 2.19 (m, 2H), 2:17 to 2:10 (m, 2H), 1.77 (m, 1H ), 1.15 (d, J = 7Hz, 3H), 1.05 (d, J = 6Hz, 3H), 1.00ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.1, 149.8, 139.9, 46.1, 38.6, 37.4, 22.1, 19.5, 18.9, 12.9 ppm. MS (EI): m / z = 27 (24), 41 (42), 55 (50), 67 (93), 83 (69), 95 (100), 110 (68), 123 (24), 137 (35), 152 (43, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:53 (m, 1H), 2:52 (m, 1H), 2:35 to 2:27 (m, 3H), 2.19 (m, 2H), 1:03 (d, J = 7Hz, 3H), 1.00 (t, J = 7Hz, 3H), 0.93ppm (m, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.6, 148.8, 139.4, 43.1, 34.8, 32.9, 22.2, 16.4, 14.0, 12.9 ppm. MS (EI): m / z = 27 (23), 41 (42), 55 (58), 67 (86), 83 (78), 95 (100), 110 (60), 123 (23), 137 (38), 152 (48, M ⁺ ).

Odor description of 2-ethyl-4,5-dimethylcyclohex-2-en-1-one: spicy, herbaceous, saffron.

Example 15: Synthesis of 2,3,4,5-tetramethylcyclohex-2-en-1-one (23)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and 3-methyl-3-penten-2-one. Fractional distillation gives 2,3,4,5-tetramethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (12%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 2.30 (m, 1H), 2.25 (m, 3H), 1.95 (m, 3H), 1.74 (m, 3H), 1:02 (d, J = 7Hz , 3H), 0.98 ppm (d, J = 6Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.2, 160.8, 129.8, 41.3, 40.3, 32.2, 20.5, 18.4, 11.1, 10.9 ppm. MS (EI): m / z = 27 (15), 41 (40), 55 (30), 67 (100), 83 (75), 95 (65), 110 (97), 123 (6), 137 (12), 152 (59, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 2.61 (m, 1H), 2.16 (m, 1H), 2.10 (m, 1H), 1.95 (m, 1H), 1.91 (m, 3H), 1.75 (m, 3H), 1.22 (d, J = 7Hz, 3H), 1.04ppm (d, J = 6Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 198.4, 157.1, 129.9, 43.2, 41.5, 34.8, 20.2, 20.1, 18.1, 10.2 ppm. MS (EI): m / z = 27 (15), 41 (41), 55 (32), 67 (100), 83 (75), 95 (64), 110 (85), 123 (7), 137 (15), 152 (55, M ⁺ ).

Odor description of 2,3,4,5-tetramethylcyclohex-2-en-1-one: spicy, saffron, leather, tobacco.

Description of the taste of 2,3,4,5-tetramethylcyclohex-2-en-1-one: medicinal, woody, pungent, bitter, cooling.

Example 16: Synthesis of 2-ethyl-3,4,5-trimethylcyclohex-2-en-1-one (24)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 3-methyl-3-penten-2-one. Fractional distillation gives 2-ethyl-3,4,5-trimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (11%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 2:35 to 2:20 (m, 6H), 1.96 (m, 3H), 1:02 (d, J = 7Hz, 3H), 0.97 (d, J = 6Hz, 3H), 0.91 ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 198.7, 160.4, 135.9, 41.3, 40.5, 32.2, 19.8, 18.5, 18.4, 13.4, 11.2 ppm. MS (EI): m / z = 29 (16), 41 (53), 55 (24), 67 (41), 81 (100), 97 (62), 109 (72), 124 (87), 137 (19), 151 (38), 166 (79, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 2.60 (m, 1H), 2:35 to 2:20 (m, 2H), 2.14 (m, 1H), 2:08 (m, 1H), 1.95-1.93 (m , 1H), 1.92 (m, 3H), 1.22 (d, J = 7Hz, 3H), 1.04 (d, J = 7Hz, 3H), 0.91ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 197.9, 156.5, 136.0, 43.2, 41.7, 34.7, 20.0, 19.6, 18.5, 18.2, 13.3 ppm. MS (EI): m / z = 29 (13), 41 (52), 55 (22), 67 (36), 81 (100), 97 (67), 109 (66), 124 (96), 137 (19), 151 (39), 166 (77, M ⁺ ).

Odor description of 2-ethyl-3,4,5-trimethylcyclohex-2-en-1-one: fresh, minty, tobacco, saffron, spicy, lovage.

Example 17: Synthesis of 2-ethyl-5,5-dimethylcyclohex-2-en-1-one (28)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 3-methylbut-2-enal. Silica gel column chromatography (eluent: cyclohexane / ethyl acetate 30/1) gives 2-ethyl-5,5-dimethylcyclohex-2-en-1-one as a colorless oil (4%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6:57 (m, 1H), 2.28 (s, 2H), 2.24 (m, 2H), 2.22 (m, 2H), 1:02 (s, 6H), 1:01 ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.7, 141.6, 140.2, 52.2, 40.1, 34.0, 28.3, 22.1, 12.9 ppm. MS (EI): m / z = 27 (5), 41 (15), 53 (12), 67 (30), 81 (17), 96 (100), 109 (20), 123 (2), 137 (5), 152 (27, M ⁺ ).

Odor description of 2-ethyl-5,5-dimethylcyclohex-2-en-1-one: spicy, lovage, saffron, apple.

Example 18: Synthesis of 2,3,5,5-tetramethylcyclohex-2-en-1-one (29)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and mesityl oxide. Fractionating distillation gives 2,3,5,5-tetramethylcyclohex-2-en-1-one as a colorless oil (5%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2.24 (s, 2H), 2.20 (m, 2H), 1.90 (m, 3H), 1.77 (m, 3H), 1:00 ppm (s, 6H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.3, 152.5, 129.8, 51.1, 47.0, 32.7, 28.3, 21.6, 10.5 ppm. MS (EI): m / z = 27 (8), 41 (15), 53 (11), 68 (32), 83 (6), 96 (100), 109 (9), 124 (2), 137 (4), 152 (34, M ⁺ ).

Odor description of 2,3,5,5-tetramethylcyclohex-2-en-1-one: tobacco, spicy, leather, animal.

Description of the taste of 2,3,5,5-tetramethylcyclohex-2-en-1-one: medicinal, fresh, spearmint, cereals, hay, clover.

Example 19: Synthesis of 2-ethyl-3,5,5-trimethylcyclohex-2-en-1-one (30)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and mesityl oxide. Fractional distillation gives 2-ethyl-3,5,5-trimethylcyclohex-2-en-1-one as a colorless oil (6%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2.31 (m, 2H), 2.23 (s, 2H), 2.21 (m, 2H), 1.92 (m, 3H), 1.00 (s, 6H), 0.93 ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 198.8, 152.0, 136.0, 51.4, 47.0, 32.7, 28.2, 21.0, 18.2, 13.5 ppm. MS (EI): m / z = 29 (8), 41 (25), 55 (9), 67 (49), 82 (47), 95 (9), 110 (100), 123 (9), 137 (1), 151 (6), 166 (36, M ⁺ ).

Odor description of 2-ethyl-3,5,5-trimethylcyclohex-2-en-1-one: tobacco, spicy, leather, saffron.

Example 20: Synthesis of 6-ethyl-4-methylcyclohex-2-en-1-one (31)

Synthesis analogous to Example 1.2, starting from ethyl 2-ethylacetoacetate and methacrolein. Silica gel column chromatography (eluent: cyclohexane / ethyl acetate 30/1) gives 6-ethyl-4-methylcyclohex-2-en-1-one as a colorless oil (15%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.71 (m, 1H), 5.94 (m, 1H), 2.60 (m, 1H), 2.19 (m, 1H), 2.12 (m, 1H), 1.93 (m, 1H), 1.40 (m, 1H), 1.36 (m, 1H), 1.15 (d, J = 7Hz, 3H), 0.93ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 201.5, 155.2, 128.8, 47.6, 36.6, 32.2, 21.8, 21.0, 11.0 ppm. MS (EI): m / z = 27 (15), 39 (22), 54 (31), 67 (11), 82 (100), 96 (59), 110 (53), 123 (7), 138 (4, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.74 (m, 1H), 5.87 (m, 1H), 2.60 (m, 1H), 2.30 (m, 1H), 2:00 (m, 1H), 1.79 (m, 1H), 1.74 (m, 1H), 1.49 (m, 1H), 1.16 (d, J = 7Hz, 3H), 0.96ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.3, 154.6, 127.6, 45.8, 34.6, 28.1, 22.8, 19.7, 11.7 ppm. MS (EI): m / z = 27 (14), 39 (21), 54 (32), 67 (9), 82 (100), 96 (46), 110 (42), 123 (4), 138 (6, M ⁺ ).

Odor description of 6-ethyl-4-methylcyclohex-2-en-1-one: green, nutty, lactonic, fruity, coconut.

Example 21: Synthesis of 4,6-diethylcyclohex-2-en-1-one (32)

Synthesis analogous to Example 1.2, starting from ethyl 2-ethylacetoacetate and 2-ethylacrolein. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 4,6-diethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (12%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.78 (m, 1H), 5.97 (m, 1H), 2:39 (m, 1H), 2.18 (m, 1H), 2.12 (m, 1H), 1.94 (m, 1H), 1.54 (m, 2H), 1.40 (m, 1H), 1.30 (m, 1H), 1.00 (t, J = 7Hz, 3H), 0.94ppm (t, J = 8Hz, 3H) , ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 201.8, 153.9, 129.3, 47.7, 38.8, 33.9, 28.2, 22.0, 11.1 ppm. MS (EI): m / z = 27 (6), 41 (12), 55 (16), 67 (16), 81 (76), 96 (100), 109 (10), 124 (31), 152 (6, M ⁺ ).

Secondary compound : ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.7, 153.4, 128.0, 46.1, 34.7, 32.0, 27.2, 22.9, 11.8, 11.7 ppm. MS (EI): m / z 27 (8), 41 (14), 55 (16), 67 (18), 81 (82), 96 (100), 109 (8), 124 (24), 152 ( 10, M ⁺ ).

Odor description of 4,6-diethylcyclohex-2-en-1-one: spicy, caraway, greasy, green.

Example 22: Synthesis of 4-ethyl-6-methylcyclohex-2-en-1-one (33)

Synthesis analogous to Example 1.2, starting from 2-methylacetessigsäureethylester and 2-ethylacrolein. Column chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate 30/1) gives 4-ethyl-6-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (35%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.79 (m, 1H), 5.97 (m, 1H), 2:42 (m, 1H), 2:37 (m, 1H), 2:09 (m, 1H), 1.52 (m, 1H), 1.45 (m, 1H), 1.39 (m, 1H), 1.14 (d, J = 7Hz, 3H), 0.99ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.4, 154.2, 128.8, 41.5, 38.7, 37.5, 28.1, 15.0, 11.1 ppm. MS (EI): m / z = 27 (14), 41 (17), 53 (20), 67 (18), 81 (100), 96 (81), 110 (9), 138 (19, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.85 (m, 1H), 5.91 (m, 1H), 2:53 (m, 1H), 2:37 (m, 1H), 2:09 (m, 1H), 1.87 (m, 2H), 1.58 (m, 1H), 1.45 (m, 1H), 1.15 (d, J = 7Hz, 3H), 1.03ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.8, 153.6, 127.9, 38.6, 35.1, 34.9, 26.7, 15.6, 12.0 ppm. MS (EI): m / z = 27 (14), 41 (16), 53 (20), 67 (18), 81 (100), 96 (78), 110 (9), 138 (17, M ⁺ ).

Odor description of 4-ethyl-6-methylcyclohex-2-en-1-one: spicy, caraway, green, watery, flower.

Example 23: Synthesis of 2,4-diethylcyclohex-2-en-1-one (34)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 2-ethylacrolein. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 2,4-diethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (15%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6:56 (m, 1H), 2:50 (m, 1H), 2:33 (m, 1H), 2.31 (m, 1H), 2.20 (m, 2H), 2:07 ( m, 1H), 1.62 (m, 1H), 1.53 (m, 1H), 1.44 (m, 1H), 1.01 (t, J = 7Hz, 3H), 0.99ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.8, 148.6, 140.3, 37.9, 37.5, 28.5, 28.0, 22.5, 12.9, 11.4 ppm. MS (EI): m / z = 27 (22), 41 (27), 55 (32), 67 (33), 81 (100), 95 (69), 110 (59), 123 (42), 137 (8), 152 (61, M ⁺ ).

Odor description of 2,4-diethylcyclohex-2-en-1-one: green, technical, spicy, coumarin.

Example 24: Synthesis of 4-ethyl-5-methylcyclohex-2-en-1-one (37)

Synthesis analogous to Example 1.2, starting from ethylacetoacetate and 2-ethylcrotonaldehyde. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 10/1) gives 4-ethyl-5-methylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (10%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.85 (m, 1H), 6:02 (m, 1H) 2.48 (m, 1H), 2.16 (m, 1H), 2.08-1.98 (m, 2H ), 1.73 (m, 1H), 1.54 (m, 1H), 1.06 (d, J = 6Hz, 3H), 0.96ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.2, 154.3, 129.2, 45.3, 44.4, 33.4, 24.1, 19.5, 10.5 ppm. MS (EI): m / z = 27 (13), 41 (20), 55 (31), 68 (46), 81 (100), 96 (31), 109 (15), 123 (6), 138 (17, M ⁺ ).

Besides the compound: ¹ H-NMR (CDCl _3, 400 MHz): δ 6.83 (m, 1H), 5.99 (m, 1H), 2:42 to 2:30 (m, 4H), 1:58 to 1:46 (m, 2H), 1:02 (t , J = 7Hz, 3H), 0.94ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.9, 153.5, 128.7, 44.6, 418, 32.3, 23.3, 14.7, 11.9 ppm. MS (EI): m / z = 27 (11), 41 (18), 55 (27), 68 (30), 81 (100), 96 (36), 109 (13), 123 (4), 138 (15, M ⁺ ).

Odor description of 4-ethyl-5-methylcyclohex-2-en-1-one: almond, fruity, cherry, cinnamon, balsamic.

Example 25: Synthesis of 3,6-diethylcyclohex-2-en-1-one (40)

Synthesis analogous to Example 1.2, starting from ethyl 2-ethylacetoacetate and 1-penten-3-one. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 3,6-diethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (26%).

¹ H-NMR _(CDCl3, 400 MHz): δ 5.83 (m, 1H), 2:32 (m, 2H), 2.22 (m, 2H), 2:16 to 2:05 (m, 2H), 1.86 (m, 1H), 1.73 (m, 1H), 1.43 (m, 1H), 1.10 (t, J = 7Hz, 3H), 0.94ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 202.0, 166.4, 124.3, 47.2, 30.6, 28.9, 27.2, 22.2, 11.5, 11.3 ppm. MS (EI): m / z = 27 (11), 41 (16), 53 (16), 67 (34), 81 (40), 96 (100), 109 (14), 124 (52), 137 (7), 152 (21, M ⁺ ).

Odor description of 3,6-diethylcyclohex-2-en-1-one: green, mint, tobacco, lovage.

Example 26: Synthesis of 2,3-diethylcyclohex-2-en-1-one (41)

Synthesis analogous to Example 1.2, starting from ethyl 3-oxohexanoate and 1-penten-3-one. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 2,3-diethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (15%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2:37 (m, 2H), 2:33 (m, 2H), 2.29 (m, 2H), 2.27 (m, 2H), 1.92 (m, 2H), 1.10 ( t, J = 8Hz, 3H), 0.94ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.2, 160.0, 136.5, 38.1, 30.1, 27.7, 22.6, 18.2, 14.2, 12.5 ppm. MS (EI): m / z = 27 (13), 41 (36), 55 (26), 67 (40), 81 (100), 95 (46), 109 (37), 124 (78), 137 (21), 152 (77, M ⁺ ).

Odor description of 2,3-diethylcyclohex-2-en-1-one: tobacco, saffron, fruity, apple, damascone.

Example 27: Synthesis of 4-ethyl-2,5-dimethylcyclohex-2-en-1-one (42)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and 2-ethylcrotonaldehyde. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 5/1) gives 4-ethyl-2,5-dimethylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (34%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:59 (m, 1H) 2.48 (m, 1H), 2.14 (m, 1H), 2:02 (m, 1H), 1.96 (m, 1H), 1.78 (m, 3H), 1.69 (m, 1H), 1.48 (m, 1H), 1.04 (d, J = 6Hz, 3H), 0.95ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.3, 149.4, 135.1, 45.6, 44.7, 33.9, 24.6, 19.4, 15.8, 10.5 ppm. MS (EI): m / z = 27 (7), 41 (31), 55 (14), 69 (55), 81 (17), 95 (100), 110 (20), 123 (18), 137 (6), 152 (9, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:56 (m, 1H), 2:37 (m, 4H), 1.78 (m, 3H), 1:47 (m, 2H), 1.00 (d, J = 7Hz , 3H), 0.90 ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.0, 148.4, 134.5, 44.8, 42.0, 32.6, 23.7, 15.8, 14.5, 11.9 ppm. MS (EI): m / z = 27 (7), 41 (30), 55 (13), 69 (50), 81 (18), 95 (100), 110 (21), 123 (17), 137 (6), 152 (7, M ⁺ ).

Odor description of 4-ethyl-2,5-dimethylcyclohex-2-en-1-one: spicy, aromatic, camphrig, floral, animal.

Example 28: Synthesis of 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one (43)

To a solution of methyl 3-oxovalerate (215 g, 1.36 mol) and isobutyl aldehyde (61.2 g, 0.85 mol) is added dropwise piperidine (7.4 g) in ethanol (20 mL) at 0-5 ° C within 20 minutes. The solution is stirred overnight at room temperature and heated at reflux for 2.5 hours. Thereafter, the reaction solution is refluxed with ethanol (600 ml), water (350 ml) and NaOH (56 g) for 8 hours, and the solvent is distilled off. At room temperature, water (500 mL) and MTBE (250 mL) are added and the aqueous phase is separated off. The organic phase is washed neutral with 2x 5% sulfuric acid and soda solution and concentrated. Fractional distillation gives 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one as a colorless oil (156.3 g, 64%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2:50 (ddd, J = 16, 4.2 Hz, 1H), 2:37 to 2:19 (m, 1H), 2.23 (m, 3H), 2:19 to 2:08 (m , 1H), 2.06 (dd, J = 16, 14Hz, 1H), 1.76 (dd, J = 2, 1Hz, 3H), 1.83-1.68 (m, 1H), 1.63-1.49 (m, 1H), 1.08 ( t, J = 8Hz, 3H), 0.92 (d, J = 7Hz, 3H), 0.91ppm (d, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.4, 160.0, 129.8, 41.4, 40.9, 34.3, 32.0, 28.4, 19.7, 19.4, 11.7, 10.3 ppm. MS (EI): m / z = 41 (30), 67 (62), 83 (19), 95 (22), 110 (100), 123 (12), 137 (28), 151 (2), 165 (8), 180 (87, M ⁺ ).

Odor description of 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one: strong, quinoline, leather, green, galbanum-like, spicy, tobacco.

Description of the taste of 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one: chemical, medicinal, fresh, woody, herbaceous.

Example 29: Synthesis of 3,5-diethyl-2-methylcyclohex-2-en-1-one (44)

Synthesis analogous to Example 28, starting from methyl 3-oxovalerate and propionaldehyde. Fractional distillation gives 3,5-diethyl-2-methylcyclohex-2-en-1-one as a colorless oil (62%).

¹ H-NMR _(CDCl3, 400 MHz): δ 2:52 (ddd, J = 16, 4.2 Hz, 1H), 2:41 to 2:34 (m, 1H), 2:33 to 2:19 (m, 2H), 2:12 to 2:07 (m, 1H), 2.02 (dd, J = 16, 13Hz, 1H), 1.94-1.82 (m, 1H), 1.76 (dd, J = 2, 2Hz, 3H), 1.46-1.30 (m, 2H), 1.07 (t, J = 8Hz, 3H), 0.91ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.0, 159.6, 130.0, 43.7, 36.6, 36.3, 28.6, 28.3, 11.7, 11.1, 10.2 ppm. MS (EI): m / z = 41 (25), 53 (14), 67 (60), 82 (13), 95 (21), 110 (100), 123 (6), 137 (21), 151 (10), 166 (84, M ⁺ ).

Odor description of 3,5-diethyl-2-methylcyclohex-2-en-1-one: spicy, leather, tobacco.

Example 30: Synthesis of 3-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one (45)

Synthesis analogous to Example 28, starting from methyl 3-oxovalerate and butyraldehyde. Fractional distillation gives 3-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one as a colorless oil (63%)

¹ H-NMR _(CDCl3, 400 MHz): δ 2:54 to 2:48 (m, 1H), 2:41 to 2:33 (m, 1H), 2:33 to 2:18 (m, 2H), 2.12-1.91 (m, 3H), 1.76 (t, J = 2Hz, 3H), 1.42-1.27 (m, 4H), 1.07 (t, J = 8Hz, 3H), 0.91ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.01, 159.6, 130.0, 44.0, 38.1, 37.0, 34.3, 28.3, 19.6, 14.1, 11.7, 10.2 ppm. MS (EI): m / z = 41 (26), 55 (14), 67 (53), 81 (13), 95 (17), 110 (100), 123 (8), 137 (31), 151 (4), 165 (7), 180 (68, M ⁺ ).

Odor description of 3-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one: spicy, green, celery, anise.

Example 31: Synthesis of 2-ethyl-5-isopropylcyclohex-2-en-1-one (48)

Synthesis analogous to Example 1.2, starting from ethyl 2-ethylacetoacetate and 4-methyl-2-pentenal. Column chromatographic purification on silica gel (mobile phase: cyclohexane Ethyl acetate 30/1) gives 2-ethyl-5-isopropylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (28%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6.70 (m, 1H), 2:53 (m, 1H), 2:39 (m, 1H), 2.20 (m, 2H), 2:16 to 2:04 (m, 2H), 1.83 (m, 1H), 1.57 (m, 1H), 1.00 (t, J = 7Hz, 3H), 0.92ppm (d, J = 7Hz, 6H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.3, 143.7, 140.9, 42.4, 41.9, 32.1, 29.9, 22.2, 19.6, 19.5, 12.8 ppm. MS (EI): m / z = 27 (9), 41 (22), 55 (18), 67 (31), 81 (33), 96 (100), 109 (33), 123 (31), 137 (4), 151 (5), 166 (36, M ⁺ ).

Odor description of 2-ethyl-5-isopropylcyclohex-2-en-1-one: fruity, mint, green, spicy, sage.

Example 32: Synthesis of 2-methyl-5-n-propylcyclohex-2-en-1-one (51)

Synthesis analogous to Example 1.2, starting from methyl 3-oxovalerate and (E) -2-hexenal. Fractional distillation gives 2-methyl-5-n-propylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (30%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6.72 (m, 1H), 2:53 (m, 1H), 2:40 (m, 1H), 2:07 (m, 3H), 1.77 (m, 3H), 1:34 ( m, 4H), 0.90 ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.3, 144.9, 135.5, 44.7, 38.1, 35.4, 32.6, 19.7, 15.8, 14.1 ppm. MS (EI): m / z = 27 (7), 41 (17), 54 (26), 69 (17), 82 (100), 95 (7), 109 (20), 123 (4), 137 (1), 152 (20, M ⁺ ).

Odor description of 2-methyl-5-n-propylcyclohex-2-en-1-one: spicy, fresh, sweet, anise, pepper.

Example 33: Synthesis of 2-ethyl-5-n-propylcyclohex-2-en-1-one (52)

Synthesis analogous to Example 1.2, starting from ethyl 2-ethylacetoacetate and (E) -2-hexenal. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 2-ethyl-5-n-propylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (41%).

¹ H-NMR _(CDCl3, 400 MHz): δ 6.67 (m, 1H), 2:53 (m, 1H), 2:43 (m, 1H), 2.20 (m, 2H), 2:10 to 2:02 (m, 3H), 1.34 (m, 4H), 1.00 (t, J = 7Hz, 3H), 0.91ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.9, 143.3, 141.0, 45.0, 38.1, 35.3, 32.6, 22.3, 19.7, 14.1, 12.9 ppm. MS (EI): m / z = 27 (7), 41 (18), 55 (15), 67 (32), 81 (23), 96 (100), 109 (22), 123 (42), 137 (5), 151 (3), 166 (27, M ⁺ ).

Odor description of 2-ethyl-5-n-propylcyclohex-2-en-1-one: aniseed, liquorice, lactonic, flower.

Example 34: Synthesis of 4-ethyl-5-n-propylcyclohex-2-en-1-one (57)

Synthesis analogous to Example 1.2, starting from ethyl acetoacetate and 2-ethyl-2-hexenal. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 4-ethyl-5-n-propylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (15%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.85 (m, 1H), 5.98 (m, 1H), 2:58 (m, 1H), 2.15 (m, 1H), 2.11, (m, 1H), 1.93 (m, 1H), 1.74-1.23 (m, 6H), 0.97 (t, J = 8Hz, 3H), 0.91ppm (t, J = 8Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.2, 154.3, 128.9, 42.4, 41.8, 37.6, 35.4, 24.7, 19.5, 14.2, 10.8 ppm. MS (EI): m / z = 27 (16), 41 (30), 55 (42), 68 (57), 81 (100), 95 (91), 109 (46), 123 (12), 137 (16), 166 (22, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 7:00 (m, 1H), 5.99 (m, 1H), 2:38 to 2:32 (m, 3H), 2:21 to 2:18 (m, 1H), 1.74-1.23 (m, 6H), 1.02 (t, J = 8Hz, 3H), 0.91ppm (m, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.2, 154.8, 128.9, 41.2, 40.7, 37.4, 32.5, 22.1, 20.0, 14.2, 12.1 ppm. MS (EI): m / z = 27 (14), 41 (26), 55 (35), 67 (35), 81 (100), 95 (76), 109 (39), 124 (12), 137 (14), 166 (18, M ⁺ ).

Odor description of 4-ethyl-5-n-propylcyclohex-2-en-1-one: spicy, aniseed, aldehydic.

Example 35: Synthesis of 4-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one (60)

Synthesis analogous to Example 1.2, starting from ethyl acetoacetate and 2-ethyl-2-hexenal. Column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 30/1) gives 4-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (19%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:58 (m, 1H), 2:59 (m, 1H), 2.13 (m, 2H), 1.88 (m, 1H), 1.77 (m, 3H), 1.65 (m, 1H), 1.51 (m, 2H), 1.25 (m, 3H), 0.95 (t, J = 7Hz, 3H), 0.90ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.4 149.4, 134.7, 42.7, 42.1, 38.0, 35.3, 24.8, 19.6, 15.7, 14.2, 10.8 ppm. MS (EI): m / z = 27 (7), 41 (36), 55 (22), 69 (52), 81 (18), 95 (89), 109 (100), 123 (28), 137 (12), 151 (12), 180 (5, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6.74 (m, 1H), 2:39 to 2:30 (m, 3H), 2:22 to 2:17 (m, 1H), 1.77 (m, 3H), 1:55 (m , 1H), 1.38 (m, 1H), 1.25 (m, 4H), 1.00 (t, J = 8Hz, 3H), 0.90ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 200.1, 149.7, 134.7, 41.2, 41.0, 37.8, 32.3, 22.3, 20.0, 15.9, 14.2, 12.1 ppm. MS (EI): m / z = 27 (11), 41 (34), 55 (21), 69 (48), 81 (28), 95 (91), 109 (100), 123 (28), 137 (16), 151 (18), 180 (7, M ⁺ ).

Odor description of 4-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one: sweet, technical, anise.

Example 36: Synthesis of 2,4-diethyl-5-n-propylcyclohex-2-en-1-one (61)

Synthesis analogous to Example 1.2, starting from ethyl acetoacetate and 2-ethyl-2-hexenal. Column chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate 30/1) gives 2,4-diethyl-5-n-propylcyclohex-2-en-1-one as a mixture of isomers in the form of a colorless oil (21%).

Main compound: ¹ H-NMR _(CDCl3, 400 MHz): δ 6:52 (m, 1H), 2:58 (m, 1H), 2:16 to 2:09 (m, 2H), 1.87 (m, 1H), 1.66 (m, 1H ). 1.54 (m, 3H), 1.40 (m, 1H), 1.32-1.18 (m, 3H), 1.01 (t, J = 8Hz, 3H), 0.95 (t, J = 8Hz, 3H), 0.90ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.9, 147.8, 140.3, 42.5, 42.4, 37.8, 35.3, 24.9, 22.3, 19.6, 14.2, 13.0, 10.8 ppm. MS (EI): m / z = 29 (21), 41 (41), 55 (70), 67 (28), 81 (100), 95 (42), 109 (89), 123 (100), 137 (59), 151 (56), 165 (26), 194 (21, M ⁺ ).

In addition to the compound: ¹ H-NMR _(CDCl3, 400 MHz): 6.68 δ (m, 1H) 2:39 to 2:32 (m, 3H) 2:24 to 2:18 (m, 3H), 1.61 (m, 1H) 1:40 (m , 2H), 1.32-1.18 (m, 3H), 1.01 (t, J = 8Hz, 3H), 1.00 (t, J = 7Hz, 3H), 0.90ppm (t, J = 7Hz, 3H). ¹³ C-NMR (CDCl ₃ , 100 MHz): δ 199.7, 148.1, 140.2, 41.5, 40.8, 37.6, 32.3, 22.4, 22.3, 20.0, 14.2, 13.0, 12.1 ppm. MS (EI): m / z = 29 (21), 41 (41), 55 (68), 67 (28), 81 (94), 95 (38), 109 (100), 123 (100), 137 (58), 151 (51), 165 (26), 194 (19, M ⁺ ).

Odor description of 2,4-diethyl-5-n-propylcyclohex-2-en-1-one: spicy, fruity, aniseed, floral, greasy.

Example 37: Perfume oil composition

The following perfume oil can be used to perfume various cosmetic products. Agrumex (2-tert-butylcyclohexyl acetate) (Symrise) 30.0 Agrunitrile (2,6-dimethyl-5-heptenyl cyanide) 1.0 Aldehyde C11 Undecanal 10% DPG (Undec-1 0-enal) 2.5 Aldehyde C12 laurin (dodecanal) 1.0 Aldehyde C14 suction (gamma undecalactone) 4.5 Allylcyclohexylpropionat 1.0 Allylheptylat 4.0 Ambrocenide® 0.1% DPG ((4aR, 5R, 7aS, 9R) octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a) (Symrise) 8.0 anisaldehyde 6.0 Anisylnitrile 1% DPG 5.0 benzaldehyde 2.0 benzyl 40.0 benzyl 60.0 Cedernblätteröl 0.5 Cinarol (2-methyl-3-phenyl-2-propen-1-ol) 2.0 Citral FF (3,7-dimethylocta-2,6-dienal) 1.0 Citronellol 950 (3,7-dimethyl-6-octen-1-ol) 20.0 Damascenone Total 10% DPG (2- (2,6,6-trimethyl-1,3-cyclohexadien-1-yl) -2E-buten-1-one) 1.0 Damascone alpha 10% DPG ((E) -1- (2,6,6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one) 3.0 Dihydromyrcenol (2,6-dimethyl-7-octene-2-ol) 5.0 dimethyl benzyl 4.0 Ebanol 10% DPG (3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol) (Givaudan) 3.0 Ethylmethylbutyrat-2 1.5 Ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde) 0.5 Eugenol (2-methoxy-4-allyl-phenol) 3.0 Eugenol acetate (4-allyl-2-methoxyphenylacetate) 1.0 Galaxolid 50% IPM (4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta [g] benzopyran) (International Flavors & Fragrances Inc.) 40.0 Geraniol 60 (2,6-dimethyl-trans-2,6-octadien-8-ol) 30.0 Hexyl cinnamaldehyde alpha 120.0 Indoflor® krist. 10% DPG (4,4a, 5,9b-tetrahydroindeno [1,2-d] [1,3] dioxin) (Symrise) 2.0 Iso E Super (2-Acetyl-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene) (International Flavors & Fragrances Inc.) 20.0 isoamyl 2.0 Isobutyl quinoline 1% DPG 8.5 Isoraldein 70 ((E) -3-methyl-4- (2,6,6-trimethyl-cyclohex-2-enyl) -but-3-en-2-one) (Givaudan) 15.0 Jasmaprunate (ethyl (2-methyl-1,3-dioxolan-2-yl) acetate) (Symrise) 1.0 Ligustral (2,4-dimethyl-3-cyclohexene-1-carboxaldehyde) 3.0 Lilial® (2-methyl-3- (4-tert-butylphenyl) propanal) (Givaudan) 20.0 Linalool (3,7-dimethyl-1,6-octadien-3-ol) 32.0 Menzanate 10% DPG 2.0 Methyl anthranilate 10% DPG 1.0 Methylcapronate 10% DPG 1.0 Methylheptin carbonate 10% DPG 3.0 Mysore acetate (4,7-methano-1H-indenemethanol) 5.0 orange oil 20.0 Oryclon® Spezial (4-tert-butylcyclohexylacetate) (Symrise) 60.0 phenylethylacetate 6.0 phenyl ethyl dimethyl carbinol 10.0 Rosaphen® (beta-methyl-phenylpentanol) (Symrise) 10.0 Rose oxide inactive 10% DPG (tetrahydro-4-methyl-2- (2-methylpropenyl) -2H-pyran) 4.0 Styrolylacetat 5.0 Pure terpineol 30.0 terpinyl 5.0 Vanillin (4-hydroxy-3-methoxybenzaldehyde) 1.5 Vertomugal 10% DPG (4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde) 8.0 Ylang MC Type Base 10.0 Ysamber® K (1,1,5,5-tetramethylhexahydro-spiro [1,3-dioxolane-2,8 (5H) -2H-2,4a-methanonaphthalene]) (Symrise) 8.0 Dipropylene glycol (DPG) 306.0

The perfume oil produced was divided into two equal parts. To exclude dilution effects, a first portion of the perfume oil was added with 0.5% by weight of dipropylene glycol (DPG), based on the total amount of the first portion of the perfume oil. The second part of the perfume oil was admixed with 0.5% by weight of 4-isopropyl-6-methylcyclohex-2-en-1-one from Example 2, based on the total amount of the part of the perfume oil. The resulting compositions were compared olfactorily.

The composition comprising 0.5% by weight of 4-isopropyl-6-methylcyclohex-2-en-1-one from Example 2 was perceived by perfumers to be more radiant and harmonious, with the floral aspects in particular being emphasized. In addition, a pleasant feeling of freshness was felt.

Example 38: Perfume oil composition

The following perfume oil can be used to perfume various cosmetic products. Aldehyde C14 suction (gamma undecalactone) 2.0 Amarocit® (6,6-dimethoxy-2,5,5-trimethylhex-2-ene) (Symrise) 3.0 Anethole Supra (4-Propenylanisole) 1.0 Apriconia base 10.0 Benzoin Siam Resin 20% BB 4.0 benzyl 1.0 Calone 1951 10% DPG (7-methyl-2H-1,5-benzodioxepin-3 (4H) -one) (Danisco Seillans SA) 1.0 Canthoxal [3- (4-methoxyphenyl) -2-methylpropanal] 10.0 Citronellol 950 (3,7-dimethyl-6-octen-1-ol) 6.0 Coumarin (2H-1-benzopyran-2-one) 17.0 Damascenone Total 10% DPG (2- (2,6,6-trimethyl-1,3-cyclohexadien-1-yl) -2E-buten-1-one) 6.0 Damascone alpha 10% DPG ((E) -1- (2,6,6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one) 4.0 Decalactone gamma 2.0 Dihydrojasmon 10% DPG (2-pentyl-3-methyl-2-cyclopenten-1-one) 0.5 Ethylene brassylate (1,4-dioxacycloheptadecane-5,17-dione) 100.0 Ethyllinalool [(6E) -3,7-dimethylnona-1,6-diene-3-ol] 45.0 Ethyl maltol 10% DPG (2-ethyl-3-hydroxy-4H-pyran-4-one) 2.0 Ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde) 3.0 Florhydral 10% DPG (3- (3-isopropylphenyl) butanal) (Givaudan) 4.0 Florosa® (4-methyl-2- (2-methylpropyl) tetrahydro-2H-4-pyranol) (Givaudan) 45.0 Geraniol 60 2,6-dimethyl-trans-2,6-octadien-8-ol 2.0 Globalide® (Oxacyclohexadec-12-en-2-one) (Symrise) 60.0 Globanone® (cyclohexadec-8-en-1-one) (Symrise) 40.0 grapefruit oil 5.0 Hedion® (Methyldihydrojasmonat) (Firmenich) 77.5 Hexyl salicylate cis-3 15.0 Hydroxycitronellal 15.0 Iso E Super (2-Acetyl-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene) (International Flavors & Fragrances Inc.) 170.0 Leafovert® 10% DPG (cis-hex-3-en-1-ylmethylcarbonate) 7.0 Lilial® (2-methyl-3- (4-tert-butylphenyl) propanal) (Givaudan) 50.0 Macrolide® Supra (15-cyclopentadecanolide) 60.0 Mandarin oil 5.0 Phenylethyl alcohol 10% DPG 2.0 Polysantol (3,3-dimethyl-5- (2 ', 2', 3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-2-ol) (Firmenich) 4.0 Prunella Type Base 10.0 Rose oxide high cis 1% DPG (tetrahydro-4-methyl-2- (2-methylpropenyl) -2H-pyran) 5.0 Sandalore [5- (2,2,3-trimethyl-3-cyclopentenyl) -3-methylpentan-2-ol] (Givaudan) 5.0 Synambran® R 50% IMP [3a, 6,6,9a-tetramethyldodecahydronaphtho [2,1-b] furan] (Symrise) 8.0 Timberol® (1- (2,2,6-trimethylcyclohexyl) hexan-3-ol) 3.0 Vanillin (4-hydroxy-3-methoxybenzaldehyde) 15.0 DPG 55.0

The perfume oil produced was divided into two equal parts. In order to exclude dilution effects, a first part of the perfume oil was mixed with 1.0% by weight of dipropylene glycol (DPG), based on the total amount of the first part of the perfume oil. The second part of the perfume oil was admixed with 1.0% by weight of ethyl-2,5-dimethylcyclohex-2-en-1-one from Example 10, based on the total amount of the part of the perfume oil. The resulting compositions were compared olfactorily.

The addition of 1.0% by weight of 3-ethyl-2,5-dimethylcyclohex-2-en-1-one from Example 10 gives an especially invigorating impression to the top notes of the composition. It will be one unexpected fruitiness towards peach implies. This will make the composition more natural and sparkling, thus completing the overall picture.

Example 39: Perfume oil composition

The following perfume oil can be used to perfume various cosmetic products. Aldehyde C11 Undecanal (Undec-10-enal) 4.0 Aldehyde C12 MNA (2-methylundecanal) 6.0 Aldehyde C18 suction (5-pentyldihydrofuran-2 (3H) -one) 1.5 allyl amyl 1.5 allyl caproate 0.5 Ambrettolide (Oxacycloheptadec-10-en-2-one) 2.0 Ambroxide (dodecahydro-3a, 6,6,9a-tetramethylnaphtho (2,1-b) furan) (Symrise) 1.5 amylsalicylate 31.5 Anethole Supra (4-propenyl anisole) 3.0 anisaldehyde 24.5 benzyl alcohol 1.5 benzyl benzoate 0.5 Caryophyllene, rect. 10% DPG 8.0 Coumarin (2H-1-benzopyran-2-one) 48.0 Damascone alpha ((E) -1- (2,6,6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one) 0.5 dimethylbenzylcarbinyl butyrate 6.0 dipentene 4.0 diphenyl 0.5 eucalyptus 1.5 Frambinone® (4- (4-methoxyphenyl) butan-2-one) (Symrise) 1.0 Geraniol Supra 2,6-dimethyl-trans-2,6-octadien-8-ol 6.5 Geranyl acetate (3,7-dimethyl-2,6-octadiene acetate) 1.0 Globalide® (Oxacyclohexadec-12-en-2-one) (Symrise) 14.5 Guajylacetat 0.5 Hedion® (Methyldihydrojasmonat) (Firmenich) 51.0 Heliotropin (3,4- (methylenedioxy) benzaldehyde) 8.5 hexyl salicylate 156.0 Ionol (2,6-di-tert-butyl-4-methylphenol) 4.0 Ionone beta ((E) -4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -3-buten-2-one) 71.0 Iso E Super (2-Acetyl-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene) (International Flavors & Fragrances Inc.) 92.0 Isoraldein 70 ((E) -3-methyl-4- (2,6,6-trimethyl-cyclohex-2-enyl) -but-3-en-2-one) (Givaudan) 30.0 Lilial® (2-methyl-3- (4-tert-butylphenyl) propanal) (Givaudan) 92.0 Linalool (3,7-dimethyl-1,6-octadien-3-ol) 69.0 Linalyl acetate (1,5-dimethyl-1-vinyl-4-hexenylacetate) 4.5 Nerol (2,6-dimethyl-2,6-octadien-8-ol) 2.5 ocimene 0.5 orange oil 68.0 Oryclon® Spezial (4-tert-butylcyclohexylacetate) (Symrise) 119.0 patchouli oil 9.5 Polysantol (3,3-dimethyl-5- (2 ', 2', 3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-2-ol) (Firmenich) 1.0 Sandranol® ((2E) -2-ethyl-4- (2,2,3) -trimethylcyclopent-3-en-1-yl) but-2-en-1-ol) (Symrise) 10.0 Styrolylacetat 14.5 Terpineol alpha 14.0 Tetrahydrolinalool (3,7-dimethyl-octan-3-ol) 0.5 Undecanon-2 10% DPG 2.0 Vanillin (4-hydroxy-3-methoxybenzaldehyde) 10.5

The perfume oil produced was divided into two equal parts. To exclude dilution effects, a first part of the perfume oil was mixed with 2.0% by weight of dipropylene glycol (DPG), based on the total amount of the first part of the perfume oil. The second part of the perfume oil was admixed with 2.0% by weight of 2,3,4,5-tetramethylcyclohex-2-en-1-one from Example 15, based on the total amount of the part of the perfume oil. The resulting compositions were compared olfactorily.

The addition of 2.0% by weight of 2,3,4,5-tetramethylcyclohex-2-en-1-one from Example 15 produces an unexpected fresh floral accord, combined with a pleasant fruitiness. Thus, the composition receives more charisma and abundance.

Example 40: Perfume oil composition

The following perfume oil can be used to perfume various cosmetic products. Ambrocenide® 0.1% DPG ((4aR, 5R, 7aS, 9R) octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a) (Symrise) 20.0 Ambroxide (dodecahydro-3a, 6,6,9a-tetramethylnaphtho (2,1-b) furan) (Symrise) 5.0 Aurelione (cyclohexadec-8-en-1-one) (Symrise) 120.0 mugwort oil 10.0 Bergamot base 80.0 Cedramber 20.0 Cistus oil 10% DPG 10.0 lemon 20.0 Coumarin (2H-1-benzopyran-2-one) 20.0 Cyclogalbanat® 10% DPG 5.0 Dihydromyrcenol (2,6-dimethyl-7-octene-2-ol) 60.0 Ebanol (3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol) (Givaudan) 15.0 Evernyl® (3-methoxy-5-methylphenol) (Givaudan) 5.0 Galbanum oil 10% DPG 15.0 Geraniumbase 20.0 Globalide® (Oxacyclohexadec-12-en-2-one) (Symrise) 60.0 Hedion® (Methyldihydrojasmonat) (Firmenich) 30.0 Hexyl cinnamaldehyde alpha 40.0 Iso E Super (2-Acetyl-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene) (International Flavors & Fragrances Inc.) 150.0 Isoraldein 70 ((E) -3-methyl-4- (2,6,6-trimethyl-cyclohex-2-enyl) -but-3-en-2-one) (Givaudan) 20.0 Krauseminzöl 10% DPG 10.0 Lavandin oil Grosso 30.0 Lilial® (2-methyl-3- (4-tert-butylphenyl) propanal) (Givaudan) 30.0 Linalool (3,7-dimethyl-1,6-octadien-3-ol) 20.0 Linalyl acetate (1,5-dimethyl-1-vinyl-4-hexenylacetate) 30.0 Lyral® 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarboxaldehyde 40.0 Mandarin oil 5.0 Clove bud oil 10.0 patchouli oil 79.5 Vanillin (4-hydroxy-3-methoxybenzaldehyde) 20.0

The perfume oil produced was divided into two equal parts. To exclude dilution effects, a first portion of the perfume oil with 0.5% by weight of dipropylene glycol (DPG), based on the total amount of the first part of the perfume oil. The second part of the perfume oil was admixed with 0.5% by weight of 2,3,5,5-tetramethylcyclohex-2-en-1-one from Example 18, based on the total amount of the part of the perfume oil. The resulting compositions were compared olfactorily.

The addition of 0.5% by weight of 2,3,5,5-tetramethylcyclohex-2-en-1-one from Example 18 gives the composition a surprising freshness character. In addition, the top notes, especially the floral and fruity aspects are particularly enhanced, so that the composition gains more expression and elegance.

Example 41: Perfume oil composition

The following perfume oil can be used to perfume various cosmetic products. Agrumex (2-tert-butylcyclohexyl acetate) (Symrise) 40.0 Aldehyde C8 octanal 10.0 Ambrocenide® 10% DPG ((4aR, 5R, 7aS, 9R) octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a) (Symrise) 5.0 Damascone alpha 1% DPG ((E) -1- (2,6,6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one) 20.0 Dihydromyrcenol (2,6-dimethyl-7-octene-2-ol) 80.0 dimethyl benzyl 15.0 Hedion® (Methyldihydrojasmonat) (Firmenich) 30.0 Herbaflorate (4,7-Methano-3a, 4,5,6,7,7a-hexahydro-5-indenylacetate and / or 4,7-methano-3a, 4,5,6,7,7a-hexahydro-6-one indenyl acetate) (Symrise) 80.0 Herbylpropionat 40.0 hexyl salicylate 100.0 Hexyl cinnamaldehyde alpha 78.0 Helvetolide® (2- [1- (3,3-dimethyl-cyclohexyl) ethoxy] -2-methyl-1-propanol-propanoate (Firmenich) 10.0 Iso E Super (2-Acetyl-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene) (International Flavors & Fragrances Inc.) 120.0 Isoraldein 70 ((E) -3-methyl-4- (2,6,6-trimethyl-cyclohex-2-enyl) -but-3-en-2-one) (Givaudan) 50.0 Majantol® (2,2-dimethyl-3- (3-methylphenyl) propanol) 50.0 Nerolione® [1- (3-methyl-2-benzofuran-1-yl) ethanone] 5.0 Oryclon ® Spezial (4-tert-butylcyclohexylacetate) (Symrise) 100.0 patchouli oil 50.0 phenylethyl 35.0 Phenoxanol (3-methyl-5-phenylpentan-1-ol) 20.0 Symrose® 50.0 undecavertol 10.0

The perfume oil produced was divided into two equal parts. To exclude dilution effects, a first part of the perfume oil was mixed with 2.0% by weight of dipropylene glycol (DPG), based on the total amount of the first part of the perfume oil. The second part of the perfume oil was admixed with 2.0% by weight of 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one from Example 28, based on the total amount of the part of the perfume oil. The resulting compositions were compared olfactorily.

After addition of 2.0% by weight of 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one from Example 28, in particular floral notes are intensified. The composition unfolds a rosy chord and is combined with a fresh naturalness and stimulating sensuality.

Example 42: Deodorant spray

ingredients Wt .-% Ethyl alcohol 96% 48.75 Deolite (dimethylphenylpropanol, 1,5-pentanediol) (Symrise) 0.25 Propellant 2.7 bar 50,00 Perfume oil composition from example 38 1.00

The smell of the deodorant spray itself as well as the odor perceived near the armpit after application of the same showed a distinctly fruity aspect, the overall impression being radiant, natural and harmonious.

Example 43: deodorant stick

ingredients Wt .-% sodium 6.5 Deolite (dimethylphenylpropanol, 1,5-pentanediol) (Symrise) 0.5 Ethyl alcohol 96% 74.3 glycerin 10.0 PPG-3 Mystyl Ether 7.7 Perfume oil composition from Example 39 1.0

Example 44: Deo-roll-on with alcohol and Symdeo

ingredients Wt .-% Propane-1,2-diol 7.00 Ethyl alcohol 96% 50,00 Ultrathix P 100 (acrylic acid / VP Crosspolymer) (ISP Global Technologies) 0.60 Deionized water 39.35 Symdeo MPP 0.50 EDTA-Na 4 0.05 Sodium hydroxide solution, 10% 0.50 Cremophor CO 40 1.00 Perfume oil composition from Example 40 1.00

Example 45: Shampoo

ingredients Wt .-% water 71.9 Plantacare PS 10 (sodium lauryl sulfate, lauryl glucoside) (Cognis) 20.0 Euperlan PK 771 (glycol distearate, sodium lauryl sulfate, cocamide MEA, laureth-10) (Cognis) 6.0 preservative 0.5 sodium chloride 1.4 citric acid 0.1 Perfume oil composition from example 41 0.1

Example 46: shower gel

ingredients Wt .-% water 77.436 Plantacare PS 10 (sodium lauryl sulfate, lauryl glucoside) (Cognis) 20,000 phenoxyethanol 0,500 sodium chloride 1,400 citric acid 0.164 Perfume oil composition from example 38 0,500

Example 47: Face Cream O / W

ingredients Wt .-% Phase A Dracorin 100 S.E.P. (Glyceryl Stearate, PEG-100 Stearate) (Symrise) 2.5 glyceryl stearate 2.0 cetearyl 2.0 Dragoxat 89 (ethylhexylisononanonate) (Symrise) 3.0 mineral oil 3.0 Neutral oil (caprylic / capric triglyceride) 4.0 Abil 350 (dimethicone) (Degussa-Goldschmidt) 0.5 tocopheryl acetate 0.3 Phase B Deionized water 77.7 Keltrol RD (Xanthan Gum) (CP Kelko) 0.1 Carbopol Ultrez-10 (carbomer) (BF Goodrich, Belgium) 0.1 glycerin 3.0 Dragocid Liquid (phenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben) (Symrise) 0.8 Phase C Sodium hydroxide solution, 10% 0.2 Phase D Dragoderm (Glycerin, Triticum Vulgare Gluten, Water) (Symrise) 0.5 Phase E Perfume oil composition from Example 39 0.3

Example 48: Anti Aging Face Cream O / W, SPF 15

ingredients Wt .-% Phase A Dracorin CE (glyceryl stearate citrate) (Symrise) 3.50 glyceryl stearate 1.50 cetyl alcohol 2.00 Softisan 100 (hardened coconut glycerides) (Clariant GmbH) 1.00 Dragoxat 89 (ethylhexylisononanonate) (Symrise) 2.00 cocoa butter 1.00 Neo Heliopan 357 (Butylmethoxybenzoylmethane) (Symrise) 1.50 Neo Heliopan 303 (Octocrylene) (Symrise) 7.50 Neo Heliopan OS (Ethylhexyl salicylate) (Symrise) 5.00 tocopheryl acetate 0.50 Xiameter PMX-0245 cyclosiloxane (cyclopentasiloxane) (Dow Corning 1.00 Disodium EDTA 0.10 Dragosantol 100 (Bisabolol) (Symrise) 0.10 tocopherol 0.10 Keltrol CG-T (Xanthan gum) (CP Kelko) 0.25 Carbopol ETD 2050 (Carbomer) (Noveon) 0.10 Phase B Deionized water 62.92 Neo Heliopan AP, neutralized with triethanolamine (disodium phenyldibenzimidazole tetrasulfonate) (Symrise) 1.36 Actipone Amla (Amalki) Fruit GW (Glycerin, Water, Phyllanthus Emblica Fruit Extract) (Symrise) 1.00 glycerin 3.50 panthenol 0.50 preservative 0.80 triethanolamine 0.40 Phase C DragoBetaGlucan (water, butylene glycol, glycerin, oatmeal extract) (Symrise) 1.00 DragoCalm (water, glycerin, oatmeal extract) (Symrise) 0.50 Color I 0.32 Color II 0.25 Perfume oil composition from example 37 0.30

Example 49: Body Lotion O / W

ingredients Wt .-% Phase A Dracorin GOC (Glycerol Oleate Citrate, Caprylic / Capric Acid Triglyceride) (Symrise) 1.50 shea butter 2.00 Dracorin CE (glyceryl stearate citrate) (Cognis) 1.00 glyceryl stearate 3.00 Sweet Almond oil 7.00 isopropyl 3.00 Phase B Biotive D - (+) - Trehalose (Symrise) 0.10 Deionized water 77.85 Amaze "XT (Dehydroxanthan Gum) (National Starch & Chemical) 0.40 glycerin 1.50 sodium benzoate 0.25 potassium sorbate 0.25 Phase C SymMatrix (maltodextrin, blackberry leaf extract) (Symrise) 0.30 Symrelief (bisabolol, ginger root extract) (Symrise) 0.10 Extrapone Aloe Vera GW (Water, Glycerin, Aloe Vera) (Symrise) 1.00 Phase D citric acid 0.25 Phase E Perfume oil composition from Example 40 0.50

Example 50: Hand and Body Cream O / W, hot-cold-processing

ingredients Wt .-% Phase A Dracorin GOC (Glycerol Oleate Citrate, Caprylic / Capric Acid Triglyceride) (Symrise) 2.00 PCL Solid (stearylheptanoate, stearylcaprylate) (Symrise) 2.50 cetearyl 1.50 glyceryl stearate 1.00 Dragoxat 89 (ethylhexylisononanonate) (Symrise) 3.00 PCL Liquid 100 (Cetearylethylhexanoate) (Symrise) 7.00 Isodragole (Triisononanoin) (Symrise) 4.00 Dow Corning 345 Fluid (Cyclomethicone) (Dow Corning GmbH) 0.50 Phase B Deionized water 72.10 Carbopol Ultrez 21 (Acrylates / C10-30 Alkyl Acrylic Crosspolymer) (Noveon) 0.20 Keltrol CG-T (Xanthan gum) (CP Kelko) 0.10 glycerin 3.00 DragoBetaGlucan (water, butylene glycol, glycerin, oatmeal extract) (Symrise) 1.50 potassium sorbate 0.10 Dragocid Liquid (phenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben) (Symrise) 0.80 Phase C Sodium hydroxide solution, 10% 0.50 Perfume oil composition from example 38 0.20

Example 51: Haircoloration, Creambase Blond with Ammonia

ingredients Wt .-% Phase A Oxowax (cetyl alcohol, oleyl alcohol, cetearyl alcohol, stearic acid) (LCW) 21.0 Ceteareth-25 4.0 Laureth-8 10.0 sodium cetearyl sulfate 1.0 Polyquaternium-6 (LCW) 4.0 water 49.3 Phase B ammonia 10.2 Phase C Perfume oil composition from Example 39 0.5

Example 52: Hair Conditioner (Rinse)

ingredients Wt .-% Phase A cetearyl 2.5 glyceryl stearate 3.0 Cutina HR Powder (Cognis) 0.5 Genamine KDM-P (Behentrimonium Chloride) (Clariant) 2.0 PCL-Liquid 100 (Cetearylethylhexanoate) (Symrise) 0.5 Phase B Deionized water 86.7 preservative 0.8 Phase C Dragoderm (Glycerin, Triticum Vulgare Gluten, Water) (Symrise) 3.5 Phase D Perfume oil composition from example 41 0.5

Example 53: Hair Conditioner (Leave-on)

ingredients Wt .-% Phase A cetearyl 3.50 cetrimonium 4.00 PEG-15 coco polyamines 3.00 Phase B Deionized water 81.40 Extrapone Henna (Water, Propylene Glycol, Henna Extract, Glucose) (Symrise) 1.00 Extrapone Jojoba (water, propylene glycol, PEG-40 hardened castor oil, 1,2-hexanediol, caprylglycol, jojoba seed oil) (Symrise) 1.50 Aloe Vera Gel Concentrate 10/1 (Aloe Barbadensis Leaf Juice) (Symrise) 0.50 panthenol 1.00 Dragocid Liquid (phenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben) (Symrise) 0.80 Desamido collagen 1.00 sodium chloride 2.00 Phase C Perfume oil composition from Example 39 0.30

Example 54: Sunscreen O / W "waterproof" with broadband UVA protection UVA / UVB balance

ingredients Wt .-% Phase A Emulsiphos (potassium cetyl phosphate, hardened palm glycerides) (Symrise) 3.50 cetearyl 1.00 Neo Heliopan HMS (Homosalats) (Symrise) 5.00 Neo Heliopan 303 (Octocrylene) (Symrise) 10.00 Neo Heliopan OS (Ethylhexyl salicylate) (Symrise) 5.00 Neo Heliopan 357 (Butylmethoxybenzoylmethane) (Symrise) 5.00 Eusolex T-AVO (titanium dioxide, silica gel) (Merck) 4.00 Abil Wax 9801 (Cetyldimethicone) (Degussa-Goldschmidt) 1.00 Silicare Silicones 41 M65 (Stearyl Dimethicone) (Clariant) 1.00 SF1550 (phenyltrimethicone) (GE Bayer Silicones) 2.00 Isoadipate (diisopropyl adipate) (Symrise) 3.00 tocopheryl acetate 0.50 Antaron-Ganex V-216 (PVP / hexadecene copolymer) (ISP Europe) 0.50 Disodium EDTA 0.10 Keltrol CG-T (Xanthan gum) (CP Kelko) 0.50 Phase B Deionized water 47.15 Neo Heliopan Hydro (phenylbenzimidazole sulphonic acid) (Symrise) 2.00 Neo Heliopan AP (disodium phenyldibenzimidazole tetrasulfonate) (Symrise) 2.00 preservative 0.70 triethanolamine 2.50 LaraCare A200 (galactoarabinan) (Rahn AG) 0.25 Hydrolite 5 (pentylene glycol) (Symrise) 3.00 Perfume oil composition from example 37 0.30

Example 55: Shaving foam

ingredients Wt .-% Phase A Deionized water 77.3 triethanolamine 4.0 Phase B Edenor L2 SM (stearic acid, palmitic acid) (Cognis) 5.3 Laureth-23 3.0 stearyl 0.5 Phase C preservative 0.8 Phase D sodium lauryl sulfate 3.0 Perfume oil composition from example 38 1.0 Extrapone Seaweed (Water, Propylene Glycol, Potassium Iodide, Fucus Vesiculosus Extract) (Symrise) 1.0 Dragosantol (bisabolol, farnesol) (Symrise) 0.1 Phase E Propane butane 4.2 bar 4.0

Example 56: Depilatory

ingredients Wt .-% Phase A cetearyl 10.0 Ceteareth-12 2.0 PCL liquid (cetearyl ethyl hexanoate, isopropyl myristate) (Symrise) 3.0 Dragosantol (bisabolol, farnesol) (Symrise) 0.1 Edenor L2 SM (stearic acid, palmitic acid) (Cognis) 1.0 Phase B Deionized water 52.2 urea 5.0 Neo Dragocid Powder (Methylparaben, Sorbic Acid, Dehydroacetic Acid, Propylparaben) (Symrise) 0.2 Phase C Deionized water 10.0 calcium thioglycolate 6.0 Sodium hydroxide solution, 10% 10.0 Phase D Perfume oil composition from Example 39 0.5

Example 57: Fabric softening concentrate

ingredients Wt .-% Rewoquat WE 18 (di (tallow carboxyethyl), hydroxyethylmethylammonium methosulfate) (Goldschmidt Rewo GmbH) 12.0 Parmetol A 26 (mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one) (Hoesch Julius) 0.1 Calcium chloride solution, 25% 0.4 water 86.9 Perfume oil composition from example 41 0.6

Example 58: Washing powder

ingredients Wt .-% Sodium metasilicate pentahydrate 48.0 sodium 15.0 Sodium carbonate peroxyhydrate 15.0 TAED / Sodium 5.0 Oxoalcohol C14-15, 8 EO 3.0 Sodium lauryl sulfate, C12 7.0 Trinopal CBS-X (derivatives of 4,4-distyrylbiphenyl) (Ciba) 0.5 protease 0.4 alpha-amylase 0.3 sodium sulphate 5.5 Perfume oil composition from example 37 0.3

Example 59: Liquid detergent

ingredients Wt .-% water 39.7 Dinatriumdistyrylbiphenyldisulfonat 0.1 coconut fatty acid 7.5 Potassium hydroxide solution 50% (Merck) 4.3 Propane-1,2-diol 5.0 Trideceth-9 12.0 Parmetol A 26 (mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one) (Hoesch Julius) 0.2 Sulfonic acid, C13-17 sec-alkyl, sodium salt 17.0 triethanolamine 2.0 trisodium 5.0 HOESCH PHOS DET 32 D (diethylenetriamine, pentamethylenephosphonic acid, sodium salt) (Hoesch Julius) 3.0 Ethyl alcohol 96% 3.0 protease 0.4 alpha-amylase 0.3 Perfume oil composition from example 38 0.5

Example 60: Dishwashing concentrate

ingredients Wt .-% sodium lauryl sulfate 31.0 Propane-1,2-diol 6.0 Ethyl alcohol 96% 7.0 Kokosglukosid 6.0 coco betaine 18.0 water 31.6 Perfume oil composition from Example 40 0.4

Example 61: Dishwashing detergent

ingredients Wt .-% Kokosglukosid 4.0 sodium lauryl sulfate 45.0 coco betaine 8.0 Ethyl alcohol 96% 1.0 water 41.8 Perfume oil composition from example 41 0.2

Example 62: Dishwasher Abs

ingredients Wt .-% sodium 35,00 trisodium 20.00 Sodium perborate monohydrate 7.00 Tetraacetylethylenediamine Sodium carboxymethylcellulose 3.00 protease 1.00 alpha-amylase 0.25 sodium 27.65 Sokalan PA 30 CL granulate (BASF) 2.00 Sokalan CP 45 granules (BASF) 3.00 Plurafac LF 403 (BASF) 1.00 Perfume oil composition from Example 39 0.10 Example 63: Bleaching agent ingredients Wt .-% decyl dimethyl 3.34 sodium lauryl sulfate 4.22 Sodium hypochlorite 12.5% 30.77 Sodium hydroxide solution, 30% 1.50 water 60.07 Perfume oil composition from example 37 0.10

Example 64: All-purpose cleaner

ingredients Wt .-% Parmetol A 26 (mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one) (Hoesch Julius) (Hoesch Julius) 0.1 trisodium 3.0 sodium lauryl sulfate 30.0 Trideceth-9 5.0 Ethyl alcohol 96% 2.0 water 59.6 Perfume oil composition from Example 39 0.3

Example 65: Toilet Cleaner

ingredients Wt .-% water 93.2 Kelzan ASX-T (Biesterfeld Specialty Chemicals GmbH) 0.5 Paraffin sulphonate, sodium salt 1.0 citric acid 5.0 Perfume oil composition from example 38 0.3

Example 66: Toilet Stone

ingredients Wt .-% C12 / 15 pareth-20 4.0 Cocamide MEA 6.0 C10-13, ABS-Na, powder 42.0 sodium sulphate 42.0 Perfume oil composition from example 41 6.0

Example 67: Soap

ingredients Wt .-% Basic soap HTS (Hirtler GmbH) 95.8 Titanium dioxide 1.0 water 2.0 Perfümölkomposition from Example 39 1.2

Example 68: room air improver in alginate gel

ingredients Wt .-% Deionized water 86.8 1,2-benzisothiazol-3 (2H) -one 0.2 Genugel CI-121 (CP KelcoGermany GmbH) 2.0 Trideceth-11 2.0 Propane-2-ol 4.0 Perfume oil from Example 41 5.0

Example 69: Room air improver aerosol, water based (w / o)

ingredients Wt .-% C12-15 Pareth-3 0.25 Deceth-8, Ziegler alcohol 1.00 Deionized water 22,50 Propellant 4.2 bar 75.00 Perfume oil from Example 39 1.25

Example 70: room air improver liquid, pump spray

ingredients Wt .-% Deionized water 90.7 Ethyl alcohol 96% 4.0 Empilan KCL 11/90 (Alcohol C12-15 11 EO) (Stockmeier Chemie GmbH & Co. KG) 3.0 Propane-2-ol 1.0 sodium 0.2 Parmetol A 26 (mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one) (Hoesch Julius) 0.1 Perfume composition from Example 40 1.0

Example 71: room air improver (pump / wick)

ingredients Wt .-% Deionized water 67.32 Sequion 40 NA 32 (polygon chemistry) 1.25 triethanolamine 0.30 Rewoderm (DiNa-ricinolamide MEA sulfosuccinate) (Goldschmidt AG) 2.33 Tego Sorb Conc. 50 (alcohol C12-14, ethoxylated (2-EO) + Zn-ricinoleate) (Evonik) 0.50 Ethyl alcohol 96% 20.00 solubilizer 3.00 Lactic acid 90% (2-hydroxypropionic acid) 0.30 Perfume oil composition from example 38 5.00

Example 72: Candles

ingredients Wt .-% candle wax 95.0 Perfume oil from Example 37 5.0

Example 73: Aroma type peppermint

ingredients Wt .-% Anethole (4-propenyl anisole) 9.0 L-menthol (natural or synthetic) 35.0 Peppermint oil Piperita type (natural or reconstructed) 20.0 Peppermint oil Arvensis type (natural or reconstructed) 30.0

The addition of 6.0% by weight of 4-isopropyl-6-methylcyclohex-2-en-1-one from Example 2 imparts an additional sweetness to the aromabase and thereby brings about a harmonization of the base.

Example 74: Aroma type spearmint

ingredients Wt .-% Anethole (4-propenyl anisole) 9.0 L-menthol (natural or synthetic) 30.0 Peppermint oil Piperita type (natural or reconstructed) 5.0 Peppermint oil Arvensis type (natural or reconstructed) 5.0 L-carvone 15.0 Krauseminzöl Cardiaca type (natural or reconstructed) 15.0 Spearmint oil spicata type (natural or reconstructed) 15.0

The addition of 6.0% by weight of 2,3,4,5-tetramethylcyclohex-2-en-1-one from Example 15 markedly improves the sensory profile of the base combined with a pleasant freshness.

Example 75: Aroma Type Wintergreen

ingredients Wt .-% Anethole (4-propenyl anisole) 9.0 L-menthol (natural or synthetic) 45.0 Peppermint oil Piperita type (natural or reconstructed) 2.0 Peppermint oil Arvensis type (natural or reconstructed) 3.0 Spearmint oil spicata type (natural or reconstructed) 1.0 Eugenol (2-methoxy-4-allyl-phenol) 7.0 eucalyptol 5.0 methyl salicylate 20.0

The addition of 8.0 wt .-% of 3-ethyl-2,5-dimethylcyclohex-2-en-1-one from Example 10 to the Aromabase causes a significant boost effect of minty notes and gives a stronger feeling of freshness.

Example 76: Aroma Type Eucalyptus

ingredients Wt .-% Anethole (4-propenyl anisole) 18.0 L-menthol (natural or synthetic) 50.0 Peppermint oil Piperita type (natural or reconstructed) 2.0 Peppermint oil Arvensis type (natural or reconstructed) 3.0 eucalyptol 15.0 eucalyptus oil 5.0

The addition of 7.0% by weight of 2,3,5,5-tetramethylcyclohex-2-en-1-one from Example 18 Aromabase causes a pleasant enhancement of the herbaceous notes and gives a refreshing mouthfeel.

Example 77: Aroma Type Cinnamon

ingredients Wt .-% cinnamic aldehyde 10.0 Anethole (4-propenyl anisole) 9.0 Peppermint oil Piperita type (natural or reconstructed) 10.0 Peppermint oil Arvensis type (natural or reconstructed) 15.0 Spearmint oil spicata type (natural or reconstructed) 8.0 Eugenol (2-methoxy-4-allyl-phenol) 2.0 L-menthol (natural or synthetic) 40.0

The addition of 6.0% by weight of 3-ethyl-5-isopropyl-2-methylcyclohex-2-en-1-one from Example 28 gives the aroma base a slight sharpness impression and, moreover, enhances the sweetness, so that the base is perceived as much more rounded and fresher.

Example 78: Aroma type ice candy

ingredients Wt .-% isoamyl 2.0 ethyl butyrate 0.5 Ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde) 2.0 Frambinone ™ [4- (4-hydroxyphenyl) -2-butanone] 0.5 L-menthol (of course) 8.0 1,2-propylene glycol 83.0 Compound of Example 15 4.0

Example 79: Toothpaste Silicabase

ingredients Wt .-% Deionized water 26.53 Sorbitol 70% 45,00 Solbrol M (sodium salt) 0.15 trisodium phosphate 0.10 saccharin 0.20 Sodium monofluorophosphate 1.12 PEG 1500 5.00 Sident 9 (Abrasive Silica) 10.00 Sident 22 S (Thick Silica) 8.00 sodium 0.90 Titanium (IV) oxide 0.50 sodium lauryl sulfate 1.50 Aroma from Example 73 1.00

Example 80: Toothpaste Phosphate Base

ingredients Wt .-% Deionized water 36.39 glycerin 20.00 Solbrol M (sodium salt) 0.15 Sodium monofluorophosphate 0.76 saccharin 0.20 Dicalcium phosphate dihydrate 36,00 Aerosil ^® 200 (silica) 3.00 sodium 1.20 Sodium lauryl sulfate (Texapon) 1.30 Aroma from Example 75 1.00

Example 81: Toothpaste calcium carbonate base

ingredients Wt .-% Deionized water 27.5 saccharin 0.2 Solbrol M (sodium salt) 0.2 Sodium monofluorophosphate 0.8 Sorbitol 70% 29.0 calcium carbonate 35.0 Sident 22 S (thickening silica) 2.5 sodium 1.3 Titanium (IV) oxide 0.5 Sodium lauryl sulfate (SLS) 2.0 Aroma from Example 74 1.00

Example 82: Mouthwash Concentrate

ingredients Wt .-% Ethyl alcohol 96% 42,00 Cremophor RH 455 5.00 Deionized water 48.67 allantoin 0.20 Sodium saccharin 450 0.10 Color L-Blue 5000 (1% in water) 0.03 Aroma from Example 75 4.00

Example 83: Mouthwash ("ready to use" with and without alcohol)

ingredients I% by weight II% by weight Ethyl alcohol 96% 10.00 - Cremophor CO 40 1.00 - Cremophor RH 455 - 1.80 benzoic acid 0.10 - Deionized water 83.48 87.57 Sorbitol 70% 5.00 10.00 Sodium saccharin 450 0.07 - Color L-Blue 5000 (1% in water) 0.10 - sodium fluoride - 0.18 Solbrol M sodium salt - 0.10 Pellitorin solution PLM (containing 10% pellitorin) - 0.15 Aroma from Example 76 0.25 0.20

Example 84: Chewing gum with and without sugar

ingredients I% by weight II% by weight Gum Base (chewing gum base) 21.0 30.0 glucose syrup 16.5 - glycerin 0.5 - Powdered sugar 60.0 - Powdered sorbitol - 40 Isomalt powdered - 9.5 xylitol - 2.0 Mannit D. - 3.0 aspartame - 0.1 Acesulfame K - 0.1 Emulgum ™ (soy lecithin, high content of phospholipids) - 0.3 Sorbitol (70% in water) - 13.0 glycerin 0.5 1.0 Aroma from Example 77 2.0 1.0

Example 85: Candy (Hardboiled Candy) with and without sugar

ingredients I% by weight II% by weight water 2.75 2.24 sugar 60.1 - glucose syrup 36.9 - isomalt - 94.98 xylitol - 2.40 sucralose - 0.03 Acesulfame K - 0.05 Zltronensäure - 0.05 Aroma from Example 78 0.25 0.25

Example 86: Instant beverage powder

ingredients Wt .-% Sugar (sucrose) 81.5 citric acid 11.58 trisodium citrate 0.70 tricalcium phosphate 0.60 vitamin C 0.66 Grindsted ^® JU 543 Stabilizer System (Danisco) 0.90 saccharin 0.56 Citron flavor, spray dried 1.75 Aroma from Example 77, spray-dried on maltodextrin (DE 18), dextrose and gum arabic, flavor charge 35% 1.75

Example 87: Odor enhancer concentrate

The following odor enhancer concentrate can be used to add base preparations to over-additive enhance the odor impression of the base formulation, for example, to form a particularly valuable fragrance and / or flavor composition. ingredients Wt .-% rose oxide 40 2,3,5,5-tetramethylcyclohex-2-en-1-one from Example 18 60

Example 88: Odor enhancer concentrate

The following odor enhancer concentrate can be used to add base preparations to over-additive enhance the odor impression of the base formulation, for example, to form a particularly valuable fragrance and / or flavor composition. ingredients Wt .-% rose oxide 10 2,3,5,5-tetramethylcyclohex-2-en-1-one from Example 18 50 4-Isopropyl-6-methylcyclohex-2-en-1-one from Example 2 40

Claims (15)

use a compound of formula (I)

or a mixture consisting of or comprising two, three, four, five, six or more different compounds of the formula (I),
wherein in each of the compounds of formula (I) the radicals R1, R2, R3, R4, R5 and
Each R6 independently has the following meaning
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, methyl or ethyl,
R3 is hydrogen, methyl, ethyl or isopropyl,
R4 is hydrogen, methyl, ethyl, n-propyl or isopropyl,
R5 is hydrogen or methyl,
R6 is hydrogen, methyl or ethyl,
with the proviso that R1 is not methyl or ethyl when R6 is methyl or ethyl
for over-additive strengthening of an odor impression. Use of a single compound or a mixture according to claim 1, wherein the single compound of formula (I) or one, several or all compounds of formula (I) is selected or each independently selected from the group consisting of the following compounds (1) to (61), preferably selected from the group consisting of the compounds (2), (4), (13), (23), (29) and (43):

Use according to claim 1 or 2 for the over-additive intensification of an odor impression selected from the group consisting of floral and / or fruity olfactory impressions. Use according to any one of the preceding claims, wherein the olfactory impression to be enhanced is not selected from the group consisting of nutty, hasyussig, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spicy and / or wherein the compound of formula (I) or the corresponding mixture imparts no odor impression selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spicey. (A) Compound of formula (I)

as defined in any one of the preceding claims or (B) mixture consisting of or comprising two, three, four, five, six or more different compounds of the formula (I) as defined in any one of the preceding claims, where (A) the compound of the formula (I) or (B) is one, several or all compounds of the formula (I) in the mixture or are each independently selected from the group consisting of the following compounds: 6-ethyl-4-isopropylcyclohex-2-en-1-one (1), 5,6-diethyl-4-methylcyclohex-2-en-1-one (6), 5-ethyl-4,6-dimethylcyclohexene 2-en-1-one (7), 2,5-diethyl-4-methylcyclohex-2-en-1-one (9), 3-ethyl-5-methylcyclohex-2-en-1-one (10) , 3,6-Diethyl-5-methylcyclohex-2-en-1-one (11), 3-ethyl-5,6-dimethylcyclohex-2-en-1-one (12), 2,3-diethyl-5 -methylcyclohex-2-en-1-one (14), 6-ethyl-4,5-dimethylcyclohex-2-en-1-one (16), 4,5,6-tri-methylcyclohex-2-ene 1-one (17), 2,4,5-trimethylcyclohex-2-en-1-one (18), 2-ethyl-4,5-dimethylcyclohex-2-en-1-one (19), 6 Ethyl 3,5-dimethylcyclohex-2-en-1-one (20), 6-ethyl-3,4,5-trimethylcyclohex-2-en-1-one (21), 3,4,5,6- Tetramethylcyclohex-2-en-1-one (22), 2,3,4,5-tetramethylcyclohex-2-en-1-one (23), 2-ethyl-3,4,5-trimethylcyclohex-2- en-1-one (24), 5,6-diethylcyclohex-2-en-1-one (25), 5-ethyl-6-methylcyclohex-2-en-1-one (26), 6-ethyl 5,5-dimethylcyclohex-2-en-1-one (27), 2-ethyl-5,5-dimethylcyclohex-2-en-1-one (28), 6-ethyl-4-methylcyclohex-2-ene 1-one (31), 4,6-di-ethylcyclohex-2-en-1-one (32), 4 -Ethyl-6-methylcyclohex-2-en-1-one (33), 2,4-di-ethylcyclohex-2-en-1-one (34), 6-ethyl-3,4-dimethylcyclohex-2-ene 1-one (35), 2-ethyl-3,4-dimethylcyclohex-2-en-1-one (36), 4-ethyl-5-methylcyclohex-2-en-1-one (37), 4, 6-diethyl-5-methylcyclohex-2-en-1-one (38), 4-ethyl-5,6-dimethylcyclohex-2-en-1-one (39), 3,6-diethylcyclohex-2-ene 1-one (40), 2,3-diethylcyclohex-2-en-1-one (41), 4-ethyl-2,5-dimethylcyclohex-2-en-1-one (42), 3-ethyl-5 -isopropyl-2-methylcyclohex-2-en-1-one (43), 3,5-diethyl-2-methylcyclohex-2-en-1-one (44), 3-ethyl-2-methyl-5-n -propylcyclohex-2-en-1-one (45), 6-ethyl-5-isopropylcyclohex-2-en-1-one (46), 5-isopropyl-6-methylcyclohex-2-en-1-one (47 ), 2-ethyl-5-isopropylcyclohex-2-en-1-one (48), 6-ethyl-5-n-propylcyclohex-2-en-1-one (49), 6-methyl-5-n-propylcyclohex-2-en-1-one (50), 2-methyl 5-n-propylcyclohex-2-en-1-one (51), 2-ethyl-5-n-propylcyclohex-2-en-1-one (52), 6-ethyl-5-isopropyl-3-methylcyclohexene 2-en-1-one (53), 5-isopropyl-3,6-dimethylcyclohex-2-en-1-one (54), 6-ethyl-3-methyl-5-n-propylcyclohex-2-ene 1-one (55), 3,6-dimethyl-5-n-propylcyclohex-2-en-1-one (56), 4-ethyl-5-n-propylcyclohexyl-2-en-1-one ( 57), 4,6-diethyl-5-n-propylcyclohex-2-en-1-one (58), 4-ethyl-6-methyl-5-n-propylcyclohex-2-en-1-one (59) , 4-ethyl-2-methyl-5-n-propylcyclohex-2-en-1-one (60) and 2,4-diethyl-5-n-propylcyclohex-2-en-1-one (61), preferably selected from the group consisting of 2,3,4,5-tetramethylcyclohex-2-en-1-one (23) and 3-ethyl-5-isopropyl-2-methylcyclo-hex-2-en-1-one (43). Fragrance and / or flavor composition comprising or consisting of (a) a compound of formula (I) or a mixture of two, three, four, five, six or more different compounds of formula (I) as defined in any one of the preceding claims, preferably as defined in claim 5,
and (B) one, two, three or more other fragrances and / or flavorings, wherein the other odoriferous and / or flavoring substances are not compounds of formula (I). The odoriferous and / or flavoring composition according to claim 6, wherein the or one, two, three, more or all of the other odoriferous and / or flavoring ingredients according to component (b) have a floral and / or a fruity odor. Odorant and / or flavoring composition according to any one of claims 6 or 7, wherein the or one, two, three, more or all of the other odoriferous and / or flavoring ingredients according to component (b) - either impart no odor impression, which is selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spicy, or mediate an odor impression, which is selected from the group consisting of nutty, hazelnut, pistachio , cocoa-like, caramel, meaty, toasted, chocolaty and spicy, whereby this odor impression is not over-additive intensified
and or
wherein the compound of formula (I) or the corresponding mixture does not impart an odor impression selected from the group consisting of nutty, hazelnut, pistachio, cocoa, caramel, fleshy, toasted, chocolaty and spicey. The odoriferous and / or flavoring composition according to any one of claims 6 to 8, wherein the constituent (b) contains no odoriferous and / or flavoring substances having a pyrazine base structure. The fragrance and / or flavoring composition of any one of claims 6 to 9 wherein ingredient (a) enhances one or more odor sensations of ingredient (b), preferably enhancing a floral and / or fruity odor impression of ingredient (b). Odor and / or flavoring composition according to any one of claims 6 to 10, wherein the total amount of compounds of formula (I) in the range of 0.0001 to 90 wt .-%, preferably in the range of 0.01 to 70 wt .-% , preferably in the range of 0.1 to 50 wt .-%, particularly preferably in the range of 0.1 to 30 wt .-%, most preferably in the range of 0.1 to 10 wt .-%, based on the Total weight of the fragrance and / or flavor composition. Perfumed and / or flavored articles comprising a fragrance and / or flavoring composition according to any one of claims 6 to 11. An article according to claim 12, further comprising a carrier or a substrate which is in direct contact with the compound (s) of formula (I) or the fragrance and / or flavoring composition. A method for enhancing an odor impression, preferably a floral and / or fruity odor impression, comprising the following step: Contacting or mixing a compound of formula (I)
as defined in any of claims 1 to 4 or 5, a mixture of two, three, four, five, six or more different compounds of formula (I),
as defined in any of claims 1 to 4 or 5,
or an odoriferous and / or flavoring composition according to any one of claims 6 to 11, with a product. Process for the preparation of a compound of formula (I), preferably a compound of formula (I) as defined in claim 5, comprising the following steps: (i) providing or preparing a compound of the formula (IV)

preferably by reacting a compound of formula (II) and a compound of formula (III) to give a compound of formula (IV),

such as (ii) reacting the compound of the formula (IV) and a compound of the formula (V),

such that a compound of formula (I) results,
wherein the meaning of the radicals R1, R2, R3, R4, R5 and R6 in the compounds of the formula (II), (III), (IV) and (V) are each the same as the meaning of the identically designated radicals of the compound of Formula (I).